Allyl Alcohol → Methyl 2-(hydroxymethyl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

A 100 mL 4-neck flask equipped with a stirrer, condenser, thermometer, gas inlet and oil bath was charged with 34.8 g of methyl α-(hydroxymethyl)acrylate, 3.4 g of 1,4-diazabicyclo[2.2.2]octane, and 0.02 g of 4-hydroxy-2,2,6,6-tetramethyl-1-oxyl as the polymerization inhibitor. Next, the temperature was raised to 95° C. and 26.2 g of allyl alcohol was added dropwise over 8 hours while stirring and blowing air into the reaction mixture, after which the reaction was continued for another 8 hours. Conversion of the methyl α-(hydroxymethyl)acrylate was 86 mol %, and the yields of methyl α(allyloxymethyl)acrylate and allyl ester with respect to the methyl α-(hydroxymethyl)acrylate were respectively 52.2 mol % and 1.0 mol %. The allyl ester content was 2.2 wt % per 100 wt % of methyl α-(allyloxymethyl)acrylate.

Provenance & Evidence