Methanol → 3-Thienylglyoxylic acid

Participants

Reaction Steps

To a mixture of ethyl thien-3-yl-glyoxylate (10 g) and 2 N-sodium hydroxide (50 ml) was added sufficient methanol to produce a homogeneous solution, and the reaction was allowed to stand at room temperature for one hour. The solution was poured into water, extracted with ether, acidified with 2 N-hydrochloric acid and extracted with ether. The combined extracts were dried and evaporated to give an oil which was triturated with benzene-petroleum ether, and the resulting solid filtered and dried (7.5 g; 88%), m.p. 63°, νmax. (Nujol) 3600 and 1702 cm-1 (CO2H), τ (DMSO-d6) values include 1.29, 2.21, 2.38 (thien-3-yl protons).

Provenance & Evidence