Acrolein → HCID 20163034, compound

Participants

Reaction Steps

A solution of o-tolylacetic acid (45.0 g.) in dry THF (300 ml.) was treated under argon at 5°-10° C. with a 1.60M solution (376 ml.) of butyl lithium. The suspension was stirred 2 hours at 5°-10° C. and then acrolein (dried over 3A molecular sieve) (20.0 ml., 16.8 g.) was added over 5 minutes. The mixture was stirred for 2 hours and then carefully treated with ice-water (1 1.) The aqueous mixture was washed with ether (200 ml.). The aqueous layer was separated and acidified to pH4 (HCl) and extracted with ether (3×150 ml.). The extracts were washed with water, dried (magnesium sulphate) and evaporated to give 3-hydroxy-2-o-tolyl-4-pentenoic acid (A) (55.2 g.), which was used without purification.

Provenance & Evidence