Dimethyl oxalate → HCID 54697150, compound

Participants

Reaction Steps

A mixture of dimethyl α-methyl-thiodiglycolate (Solladie-Cavallo, Bull. Soc. Chim. Fr., 437 (1968)) (10.2 g, 53 mmoles) and dimethyl oxalate (9.4 g, 79 mmoles) in methanol (25 mL) is added slowly to a solution of sodium (3.8 g, 165 mmoles) in methanol (35 mL) under argon and maintained at 10°-15° C. with an ice bath. After the addition, the mixture is slowly heated to reflux for 1 hour, then cooled and concentrated under reduced pressure. The precipitate is filtered off, rinsed with ether, air dried, dissolved in water and acidified with 4N hydrochloric acid. The precipitate is filtered off, rinsed with water and dried to afford the product (6.8 g); mp 116°-117° C.

Provenance & Evidence