Natural Science Forum / Chemistry / Organic Synthesis / October 2003

If you do a low-temp epoxidation of allyl acrylate with 1 eq. of
peracid in DCM in presence of bicarbonate (solid), it should go to the
allyl and leave acrylate intact.

The acrylates are usualy made by normal esterification by refluxing
the acrylic acid with acolhol in presence of catal. amount of acid and
radical inhibitor. Please do not forget to add the inhibitor into the
receiving flask during the distillation, also do it at vacuum at
moderate temperature - to avoid polymerisation.

Also, acryloyl chloride is commercial, although expensive. Using
conventional bases (lutidine, NEt3, iPr2NEt, pyridine etc) gives a lot
of black impurities. The alternative which worked for me was to add
excess of acrylonitrile as a co-solvent -it serves as a neutral HCl
scavanger (forms 3-chloropropionitrile). The disadvantage was that the
product contained a trace of a cyanoethyl ether from the alcohol
addition to acrylonitrile.

As far as finding acrylate stuff which does not stink and is not
lachrymatory, I think you are asking far too much.
(Acrylonitrile is particularly unpleasant.)