Carbon Dioxide → 3-Benzyloxy-2-methyl-benzoic acid

Participants

Reaction Conditions

Reaction Steps

232.7 g of 2-benzyloxy-6-chlorotoluene (232.7 g, 1.0 mol) are subjected to a Grignard reaction with 26.7 g (1.1 mol) of magnesium turnings in 550 ml of THF. The brown-black solution of (3-benzyloxy-2-methylphenyl)magnesium chloride in THF formed therefrom is stirred until cold by means of an ice bath at 0° C. CO2 gas is passed into the stirred reaction mixture slowly such that the temperature does not exceed 10° C. The solid suspension in THF formed therefrom is hydrolyzed with cooling by slow addition of 50 ml of water and 445 g (1.2 mol) of hydrochloric acid (10% strength). The hydrolyzed reaction mixture is diluted with 430 g of xylene. The phases are separated and the organic phase is washed with 100 g of water. The product-containing organic phase separated off is distilled until the bottom is free of THF. The bottom is then stirred at 0° C. until cold. The crystallized product is filtered off and washed with 50 ml of xylene. After drying in vacuo, 152.3 g of 3-benzyloxy-2-methylbenzoic acid are obtained. This corresponds to a yield of 62.9% of theory.

Provenance & Evidence