I think Novozyme-435 may help for typical esterifications. The reaction condition are temperature at 60C and it should never cross beyond, usually t-BuOH is the solvent system used. My personal experience was with fatty acid esterification with propargyl alcohol.

Please remember, this reaction works for acid+alcohol esterifications, i.e., we can choose methacrylic acid and propargyl alcohol.....as reactants

If it works please reply me....

DMF and dichloromethane should work well for your reaction. Also, methyl tert-butyl ether is regarded as safer alternative to diethyl ether due to its lower tendency to form peroxides. Some reactions (e.g. Grignard) don't work well in TBME but there shouldn't be any problems in your case.

I recommend to use THF or dichloromethane as solvents, since they are adequate to this kind of reaction. Triethylamine is usually used as base to quench the formed HCl, and avoid the hydrolysis of your ester, and other side reactions of it. In some cases, you can skip TEA, but I recommend to use it in your reaction.

The solvent must be stable under the acyl chloride conditions, i.e. it cannot have groups such OHs or NHs to react with your acyl chloride.

THF would work. Conditions: TEA ( usually in excess), alcohol and acid chloride in 1:1 ratio. 0 deg to RT under Nitrogen for 12h will work.

Thank you very much Vijay, Dragan, Haitao, Jaoa and Subramani for all your helpful answers! :)

Vijay, is Novozyme-435 an enzyme? I actually wanted to follow an existing protocol because I just really need the propargyl methacrylate for a lot more steps and I don't really have the luxury of optimizing conditions to synthesize it.

Dragan, Haitao, Jaoa and Subramani, I'll check on those solvents! Actually I read the some literature regarding how they synthesized the propargyl methacrylate and they needed to do flash chromatography further to purify it. The things is our lab is mostly a tissue engineering lab so we don't really have material characterization equipment like FTIR, HNMR, etc for our disposal for me to really check the purity. I just have a few additional questions, if it's okay.

(1) how do I monitor the reaction using thin layer chromatography as the reference you gave me Haitao indicated?

(2) is it possible to purify the product without flash chromatography? Because another procedure I read stated they used flash chromatography. Are there disposable flash chromatography columns available already that don't require me to buy glassware and silica, etc. ? Is it expensive to purchase rotary evaporator apparatuses?

(3) And would you know why is it necessary to do under N2?

Acid chlorides are highly moisture sensitive. They would react with water and get converted to corresponding acids which are not as reactive as acid chlorides are towards esterification reactions. Also If your solvent is not dry again the same problem will come in to picture. Precipitation will help. Esters are less polar compared to the alcohol and so it is possible that you can use a mixture of solvents to precipitate your compound. choice of the solvent depends on the compound.

Since you lack basic equipment and have no experience with organic chemistry, I believe it would be best if you could "outsource" - contact someone from the the chem department of your uni and ask them for help.

Yes, Novozyme-435 is an enzyme.

It's fine, the suggested conditions with reports are preferable.

All the best.

1) If you don´t have any instruments you can make TLC and see if you have the corresponding elution pic of the final product.

2) You can always purify your ester by precipitation.

3)You can use THF or DMF for synthesise your ester.

4) Under N2 you reduce the reaction between h2O and acid chlorides.

I just would like to point out that DCM (dichloromethan) is sometime stabilized with alcool and in that case not suitable for your usage.

DMF not simple to separe, and THF miscible with water, you have to include water wash to eliminate TEA/HCl, also I would prefer MTBE or Diisopropylether.

You do not have to follow carefully your reaction because optimisation yield is not your objective, also perform the reaction and eliminate the excess of reagent (acid chloride) by wash with base, should eliminate acid derivative, then concentrate organic phase but evaporator is mandatory.

This synthesis is also described with THF as solvent:

Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, p. 1138 - 1146

NB

1- acid chloride are moisture sensitive, but react more rapidly with alcohol than with water or hydroxyde ion see Menalda Rec Trav Chim , 1930, vol 49 p967 about the Schotten Baumann reaction

2- yes, dichloromethane stabilised with ethanol is not the proper choice use dichloromethane stablised with amylene (but not for olefin metathesis, of course)

Dichloromethane is the best for these type of reaction. But problem may arise during post reaction process on quenching and separation of organic layer. The aqueous and organic layer may form ~ densities and difficult to separate. you can get diethyl ether from other suppliers too, but distill the solvent before use.

The alcohol itself will act as an solvent. Without solvent you can carry out the reaction with stirring

Hello,

You should use Chloroform as a solvent with triethylamine as a base to mop up the acid, please look up Schotten-Bauman conditions. 

 For synthesizing an ester from an alcohol and acyl chloride you can use benzene as a solvent.