Science topics: Organic Chemistry Synthesis
Organic Chemistry Synthesis - Science topic
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Questions related to Organic Chemistry Synthesis
In the structure of many drugs, there is a carboxylic group
What is the significance of this group? Why should it exist in the structure of a drug?
Do you know any article or book or reference about this subject?
Thanks a lot
What kind of functional groups do we need to insert by the synthesis in organic chemistry to have anti-cancer activity in perspective?
I added 0.02gr of AIBA initiator to a 100 ml of a water solution of 5gr vinyl imidazole (distilled under reduced presuure), and purged with N2 for at least 1 hr under stirring. Then I put the container in water bath of around 70 degree centigrade. The reaction was followed under stirring and N2 atmosphere.The colour of the solution changed from white to dirty yellow.After 4 hr I let the solution cool and then I poured it into acetone bath.
However Nothing precipitated.Could you please help me what is the problem? How can I understand polymerization has been done or not?
how can i get pure compound of HEEP with 99.90% purity from Piperazine+2-Chloro ethoxy ethanol, i am trying product distillation but getting some impurities in small amount i.e 0.5% and getting on related impurity HEP(hydroxy Ethyl piperazine), please help me by providing process /article about HEEP?
Is there any effective method to reduce oxidation effect of nitrous acid (HNO2)
as it is converting my diazo compound into tars while diazotizing it,affecting the results of my final product.
Below attachment is my diazo compound.
Suggestions will be highly appreciated.
Is there any possibility of nucleophilic aromatic substitution of hydroxyl group directly without the presence of sulfonic group etc ???
kindly suggest me??
It is taught that oxidation of the benzylic carbon (Only if it contains 1 hydrogen+) will oxidize it to carboxylic acid using Na2Cr2O7 or KMnO4 with heat. but what about cyclic compounds like these 2?
In the first picture you can see two compounds X and Y, that by oxidizing them it leads to the same compound (Phtalic acid), but why? Compound Y, has 1 benzylic hydrogen from top side only, so it got oxidized, what happened to the other side? (down) or in general what happens to the " Leaving group " that gets cleaved in that matter?
Like I know if it's an alkyl oxidation, it usually gets oxidized to CO2, but here it's different, since it contains a carbonyl in the cleaved off chain.
Same in the second picture, only the top part has benzylic hydrogen, the lower part of the benzene has quartenary carbon and it should not get oxidized.
Can someone clear this reaction for me please?
Thanks a lot!
What is the most feasible method to synthesise benzoxazole from aminophenol?
i had tried with carboxylic acid derivative in the presence of PPA as a solvent,
but i am looking for some more feasible procedures and methods??
Suggestions would be appreciated.
I'am looking for way to coat my 0,5 um carboxylated polystyrene microparticles with D-mannose. Is there a protocol out there, that I've missed or something else I could use?
I would really appreciate the help.
difference between folin-denis and folin-ciocalteu is lithium sulfate and bromine.
preparation method of folin-denis : mixing sodium tungstate , phosphomolybdic acid and phosphoric acid (2hr under refluxing ).
preparation method for folin-ciocalteu : mixing sodium tungstate , sodium molybdate , phosphoric acid and conc. hydrochloric acid (10 hr under refluxing ) then add lithium sulfate and bromine .
can I prepare folin-denis by mixing sodium tungstate , sodium molybdate , phosphoric acid and conc. hydrochloric acid (10 hr under refluxing ) or not ?
can I replace phosphomolybdic acid by sodium molybdate and conc. hydrochloric acid and increase reflux time to 10 hr ?
I was previously using one of the strong base NaOH in order to convert it into sodium naphtholate (as my compound's physical appearance is in flakes form)
then at the coupling stage with diazonium chloride,
which i assume that my diazonium chloride is reacting at that NaO group (after converting 2-naphthol into sodium naptholate) on the compound.
So, how can i couple my diazonium chloride at the 1st/Alpha/Para Position of the following compound???
Suggestions Required On How Can I Make Below Compound Reactive ?
Basically,I Want To Couple This Compound With The Other (Which Is Highly Reactive).
I Have Tried Converting In Sodium Salt And Dispersing It By Some Dispersants And Solvents But That Doesn't Providing Me The Desirable Results.
Comments And Suggestions Will Be Highly Appreciated.
How can I attach an amine group (-NH2) to a carboxyl group (-COOH)? What are the experimental conditions, such as temperature, atmosphere, pH etc? I want to attach mPEG-NH2 to α-Lipoic acid in water solutions.
can anyone please suggest me how to sulfonate aromatic benzene ring in para position and instead of ortho position ?
On Which factor this position alteration depends?
Kindly please suggest me???
how to produce an intensely coloured molecule with a conjugated azo linked (single/double/ single/ double bonded) structure, and avoid missing conjugated azo link in a structure.
I am trying to make a benzoxazole compound.
Is it possible to carry out the condensation with acetic acid?
o-amino phenol condensation with thiopene2,5 di-carboxylic acid?
can I carry out condensation in polar solvents?
I have synthesized coumarin derivatives and one of the characterization is using UV-Vis. Since I don't have the standard for the synthesized compound, do I still need to run the standard for UV-Vis before I run my synthesized compound? Thanks in advance.
I've tried making this compound from 3-oxo-2-phenylbutanenitrile and 2-(iodomethyl)-3-vinyloxirane under various conditions, with various bases. Tried it with HMPA and tBuLi first but formed the kinetic enolate and thus got the wrong regiochemistry. Then I tried (without HMPA) triethylamine, cesium carbonate, sodium phosphate, potassium tert-butoxide, and TBD, but none of those worked either. Mostly the enolate opened the epoxide rather than displacing the bromine. I then tried the catalytic Finkelstein reaction in acetone, but that did not seem to work either. (epoxide still opened) Maybe there is another route?
I am trying to synthesize the enol triflate of 2-methylcyclohexanone using iPr2NMgBr asbase, and PhNTf2 (N-phenylTriflimide). I observed a lot of UV active spots in my TLC,which I guess comes from the Phenyl part. Also, I saw 3 spots on KMnO4 stain. Not sure which one to isolate.
Also, the original procedure does a "bulb-to-bulb" distillation, but we don't have that. I tried a normal distillation, but couldn't find any product (from NMR) in the distillate.
1. Why are there so many spots in the TLC? Should I expect my product tobe UV active?
2. Is that volatile enough that it enters the vacuum pump?
Has anyone experienced any such similar issues?
Any suggestions are appreciated.
i have prepared schiff base with aldehyde and amine (1:1) ratio,by using ethanol as solvent and 2 drops of acetic acid as catalyst,but i got an oily product.how can i get a solid product and with this i have do metal-ligand complex.
Because if we perform IR or NMR spectral analysis, amide bond in DMF (Dimethyl formamide) may interfere the amide bond formed during the reaction.
What would be other better methods for the characterization?
I'm trying to sulfonate diphenic acid using trimethylsilyl chlorosulfonate to obtain a water soluble form of diphenic acid by forming the corresponding sodium or potassium salt. I tried using the procedure described by the Ivan et. al in 2017 (DOI: 10.1039/c7sc00430c). But it is not working for diphenic acid. Could anyone suggest or direct me to a procedure that I can use for the sulfonation of diphenic acid using above reagent ?
i'm trying to do aldol of acetaldehyde with isatin at gram scale and i found proline catalyzed reaction is not very effective for large scale. i'm not looking for a stereocenter. do any one know to scale up this reaction? this is my initial step and would require at least 1-1.5 gm of product
i have tried doing bromination of acetyl acetone using NBS and AIBN in CHCl3. i did not get the product. I have also tried with Br2 in AcOH. but there was very less product(17%). Please suggest me a proper procedure for the same.
One of my references includes a procedure using excess amount(5eq.) of hydrogen peroxide(H2O2). (with NaOH 0.5eq. in methanol)
I usually quench it during workup with sat. sodium thiosulfate(Na2S2O3) solution, but this reference didn't include this reductive quenching.
As this quenching is pretty exothermic, this process might not be necessary if most of H2O2 stay in aqueous layer unlike acetic acid dimerization.
In addition, my substrate doesn't possess any other labile functional groups to H2O2, and the only potential problem may occur here is decomposition due to heat.
(I also observed that there was white powder at the bottom of the workup funnel(aqueous layer) generating heat and dissolving into the layer when sodium thiosulfate solution was poured.)
Do you guys use Na2S2O3 whenever using excess H2O2? (especially in gram-scale)
I wonder how others handle that.
Thanks in advance!
I have synthesized a novel spiropyran which showed two peaks located at 534nm and 576nm upon irradiation of 254nm UV light. However, When I irradiate the solution of the same compound in acetonitrile by 366nm UV light, it gives me a single peak corresponding to 577nm. I have carried out DFT optimization in ACN, which suggests that the relative energy difference between closed SP and TTC form is -18.03kJ/mol while that of TTT as -15.94kJ/mol. This suggests that TTC is the most stable conformer and it is reported that TTT gives the bathochromic shift in acetonitrile solutions. My question is since the wavelength upon 366nm irradiation correspond to the TTT form peak in an earlier case, can it exist after 366nm as well?
Based on some literature reviews...
Mostly, alkylation of amine groups are done by using suitable alkyl bromide (R-Br) and potassium carbonate.
involve the usage of alkyl p-toluenesulfonate (R-pTS) for N-alkylation.
Is it possible for me to use alkyl p-toluenesulfonate to N-alkylate the isoindigo? Or there are some restriction during N-alkylation, that alkyl bromide is preferred than using the p-toluenesulfonate?
So far I haven't come through any papers using R-pTS for isoindigo and R-Br for carbazole. Is there any reason? why?
Or am I miss out somethings important about N-alkylation?
-Tried using anhydrous chloroform
-Tried both NBS and recrystallized NBS (though, the recrystallized NBS has a slight yellow tinge for some reason)
-The procedure I've been following for the most part is to heat the reaction to 60C. I've monitored it by TLC to completion, but I'm getting incredibly low yields.
-I've tried letting it run a room temperature for about 24h, and still had low yields.
So it is a well known fact that boron containing catalysts including boric acid are perfect choices for amide formation. however, my question is if anyone knows whether boric acid would still be useful if i wanna synthesise some amide in the aqueous media.
I perform the synthesis in a ethanol-water mixture under N2 at 70 C
I have a compound contain both phenol and secondary amine groups. The amine group will act as nucleophile in the next reaction and the phenol groups will compete with the amine group in the nucleophilic process. I'd like to protect the phenol groups with TMSCl or any other kind of protecting groups before the nucleophile reaction. What kind of reagent should I use and what conditions should I apply to protect phenol groups without affecting the amine group?
I am using thiophosgene to convert primary aromatic amine to isothiocyanate in a biphasic solvent system (chloroform/water). Under these conditions tert-butyl ester in my starting material is cleaved. I am looking for a milder route to do this conversion that will retain the ester.
I am trying to do Mukaiyama Aldol Addition to introduce trifluoro-ethylidene to alpha position. But the reagent (trifluoro acetaldehyde) has boiling point -20°C. I purchased it as 75% technical grade in water (I believe its hydrated form of ketone and its promised to be stable). And I have to dry it somehow. Do somebody have any experience with drying such a volatile compounds? I have to probably destilate it (from P2O5??) and bubble it into my reaction which would be cooled to -70°C. I have only 25 ml of the hydrated aldehyde.
Is it possible for me to alkylate my compound with the present of dioxaborolane in my compound?
Most papers get their compounds alkylated first (as shown in the attachment).
What I intend to do is to get my step4 done first, followed by step3. This is because I ordered my alkyl chains late..><
If it is possible to run, did I need to change any reaction condition?
Hello All, I was synthesizing chalcone from 4-hydroxcy acetophenone and 9-anthraldehyde in ethanol for about 8 hours stiring at room temperature monitoring through TLC. I know chalcone synthesis is very sample one and have been synthesize variety of chalcone but i didnt get my product in this case.
Hi, I am trying to do a reaction between aromatic amine and aromatic ketone. First i thought it will be a straight forward reaction with some acids as catalyst. But it seems a bit difficult to carry this rxn. Should I try to change Ketone to aldehyde? and if yes, then how, only if it's necessary. Is there any direct reaction between aromatic amine and aromatic ketone?
I have trifluoroacetamide protecting group in my structure and I want to deprotect it under basic condition. There is also one ester in my structure. Is it possible to deprotect the trifluoroacetamide by base and not cleaving the ester? Any suggestion on how to reduce the possibility of cleavage?
I have been looking for 2-Chlorohexanoic acid (CAS No. 29671-30-5) for a while, writing to different suppliers without any positive results. I would like to get the L-isomer, but if it isn't available I would still use the racemic mixture.
Does anyone know of a provider?
I am looking to synthesize POCl3 from PCl5 and B(OH)3. I believe this to be an industrially used process, but I cannot find any recipes for preparation. Any help would be very much appreciated! Thank you.
I have synthesized a sodium sulfate surfactant. The starting material is soluble in CDCl3 and has a nice NMR spectrum. When i try to NMR my product in CDCl3 there was zero analyte (this is important because the starting material should have shown up if it was present). When I NMR the surfactant product in d-DMSO I get what looks like a mixture of starting material and product peak shifts... could my surfactant be decomposing/reacting in DMSO? It is not soluble in anything else besides methanol and EtOAc/hexanes and pure via TLC. Thanks!
I have tried with N-methyl isatin sarcosine and chalcone togather dumped in ethanol and heated for 900C as reported procedure but i didn't get product. If any special condition have to be adopted for formation of azomethine ylide other than adding chalcone. Please suggest any condition to get reproducipility of product.
I am doing aldol condensation of cyclicketones with p-Hydroxybenzaldehyde. The reaction yield is found to be very low when I am using base catalysed aldol condensation. I want to know the easiest metod for the aldol condensation of cyclic ketones with 4-Hydroxybenzaldehyde.
I've recently found and interesting synthetic route to diaryl thioethers, using trifluoromethanesulfonic anhydride (1st reaction in attached file).
I wonder if it would be possible to perform similiar procedure using fenol derivative (4) instead of thiolate(2).
Could the phenol be substituted with ester groups, or would they disturb the reaction with triflates?
Thank you for your interest and help.
At presently I am preparing gold potassium cyanide in the following method
Step 1: Preparation of Aqua regia
Step 2: Dissolving gold in Aqua regia
Step 3: preparation of fulminating gold
Step 4: fulminating gold to gold potassium cyanide
I want to know the more simple route to produce gold potassium cyanide in cost effective way.
I would like to know whether any software for molecular modelling is available for free? Because my stream is organic chemistry, synthesis, I just need this as a reference and I'm a little concerned about spending a fortune on this!
Thank you all :)
I need to develop a paper based assay to determine urinary creatinine levels. Since creatinine is a small molecule, I need to conjugate it to a protein like BSA to make it suitable for the assay.
Has anyone successfully able to conjugate creatinine to BSA ?
I have prepared DNS as per the recommended Miller protocol. I have a sample which is acidic pretreatment hydrolysate. Once this is added to the DNS reagent, the sample immediately precipitates thus rendering the assay useless. Any idea why this could be happening? Is there a workout?
Does anyone know about the synthetic procedure for 2,6-Diformyl-4-methylthiophenol ?
I have gone through a no of literature to find the synthetic procedure to prepare this compound using sci-finder ,unfortunately i did not get it .can u please help me to provide any reference of procedure to get this.
Does anyone know of synthetic procedure for Cyanocobalamin impurities?
I am interested in viewing the Synthetic procedure for Cyanocobalamin impurities. Please anyone can help me out. More information please find in the attachment.
Thanks and regards,
I tried with bromine and iron, bromine in CCl4 but in both cases my aldehyde peak is gone and made some unidentified product. I tried with bromine and aluminum chloride and got monobromination. I added excess reagents to push for dibromination but not successful. Is there anybody who can give me some suggestion. Any help will be highly appreciated.
A chichibabin reaction of aromatic aldehyde with aromatic ketone and ammonium acetate was charged in acetic acid. Upon completion of reaction, it was washed with cold water. After filteration, the obtained precipitates were found not soluble in DCM, dioxane, benzene, THF, Acetic Acid, MeOH, ETOH, DMSO, DMF,ETOAc, Hexane. Could someone be kind enough to guid me how to make it solubilize so that i can moniter it on TLC for purity purpose? Thanks in advance.
A similar reaction with a t-butyl substituent on the 2-position on the phenol is complete in 1 hour without a solvent at 105 degrees C. It also works by refluxing overnight in ethanol. These methods were tried but not successful. Reflux or heating for a longer time didn't work.
I am trying to attach N-Boc-3-bromopropylamine to both of the phenols of 7-hydroxycoumarin dimer with no success. I have tried K2CO3 in DMF at 80C, Cs2CO3 in DMF at 60C, TEA in DMF at 80C, DMAP in DMF at 80C & 110C but have not formed the desired product in any of these conditions and have seen significant side reactions. Does anyone know a set of conditions I should try (especially varying the solvent used as I have only used DMF)? I have attached the structure of the desired product.
I've been having trouble trying to purify 3-methylnona-1,8-dien-3-ol from a grignard reaction utilizing vinylmagnesium bromide. There is a file attached the shows the synthetic scheme. I'm not completely sure what is going wrong, but I obtain about 6-7 spots on TLC after the reaction is quenched and worked up. Has anyone had trouble with side reactions during grignard and ketone reactions? Any advice helps! Thank you!
I need to oxygenate an aromatic methyl ketone, following Dong's procedure (ACIE 2012, 51, 13075).
Using 4-methoxy- and 4-bromo-acetophenone [Pd(OAc)2, BTI, DCE, 80ºC], I get good yields of the compounds where the OH has entered alpha-carbonyl instead of ortho carbonyl.
Will appreciate any clue to change the reactivity toward the ortho acylphenols.
Thanks in advance!
I synthesized furfuryl alcohol using furfural and NaOH, and the reaction of it is autoredox reaction. I have synthesized furfuryl alcohol twice. Initially, I cooled furfural using ice bath and then i have added NaOH . In the first reaction I added NaOH when temperature of furfuryl alcohol is 7 oC and second reaction I added NaOH when it's 0 oC. why is furfuryl alcohol were obtained higher in 0 oC than 7 oC?
I have used Zn and %2 HCl but the amount of the substance is poorly. I didn't detect with TLC method.
I have stired well. Reaction temperature is ~75oC. The amount of zinc used in reaction is ten times more than substance. However i have read paper about nitroimidazole reduction with Zn, there are points that I can not do on this topic.
I appreciate if you can help me.
I am using DMAN to attach acrylic group to my compound.Presently after the reaction, I am diluting my reaction mixture by ethyl acetate and washing the organic layer by saturated Sodium bicarbonate solution for 24 hours. Still I find there is unreacted DMAN left (from NMR). I cannot wash the mixture with sodium hydroxide solution as it may react with my compound. Was can be the possible work up then?
I'm planning a synthesis to attach a functional group to benzene. All the protocols I've read utilize t-butyllithium in the process.