Ethanol → 2-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

Ethanol free sodium ethoxide was mixed with 200 ml. of toluene and cooled to 0°C. A solution of p-methoxybenzaldehyde, 56.0 g. (0.412 mole), and ethyl chloroacetate, 50.5 g. (0.412 mole), in 200 ml. of toluene was added at such a rate that the temperature remained below 10°C. After stirring at 24°C. for 16 hours, the mixture was washed twice with 400 ml. portions of water and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow liquid of about 80% purity (81.2 g.). The liquid solidified on standing at 5°C. and was further purified by washing with a small volume of cold ethanol to give pale yellow crystals of ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate having a melting point of between 40° and 43°C.

Provenance & Evidence