2-Hydroxy-p-toluic acid → HCID 14519881, compound

Participants

Reaction Steps

A two-phase mixture of 45.6 g (0.3 mol) 4-methylsalicylic acid, NaOH (36 g, 0.9 mol), benzyl bromide (154 g, 0.9 mol) and tetrabutylammonium bromide (10 g, 30 mmol) in water (200 ml) and CH2Cl2 (200 ml) was stirred at room temperature for 3 hours. The layers were separated and the CH2Cl2 was removed from the organic fraction. The residue was dissolved in a mixture of ethanol (250 ml) and 2N NaOH (50 ml), and the mixture was heated under reflux for 30 min. The ethanol was removed under vacuum and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was separated and acidified with dilute HCl to give a precipitate of 4-methyl-2-phenylmethoxybenzoic acid (65.3 g, 90%) m.p. (MeOH aq) 105°-107° C. Anal (C15H14O3) C,H,O.

Provenance & Evidence