DARZENS GLYCIDIC ESTER CONDENSATION

Benzaldehyde, acetophenone, and isobutyrophenone were condensed with the methyl, ethyl, isopropyl, and t-butyl esters of chloroacetic acid. The glycidic esters formed were analyzed for cis/trans isomer ratios. The chlorohydrin from acetophenone and t-butyl chloroacetate was treated with base in the presence of p-nitrobenzaldehyde and found to give a mixture of glycidic esters resulting from cyclization and from dealdolization and condensation with the p-nitrobenzaldehyde. A new mechanism for the Darzens glycidic ester condensation is proposed. © 1969, American Chemical Society. All rights reserved.