p-Phenylenediacetic acid → 1,4-Benzenediethanol

Participants

Reaction Steps

Borane-methyl sulfide complex (2M solution in tetrahydrofuran, 80 mL) was added over 20 min to a stirred solution of 2,2′-(1,4-phenylene)diacetic acid (10.20 g) in tetrahydrofuran (100 mL) cooled in an ice bath. After 16 h, the reaction mixture was carefully quenched with methanol (40 mL). The solution was evaporated in vacuo and the resulting gum was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The ethyl acetate solution was separated, dried over magnesium sulphate, filtered and evaporated in vacuo to give the subtitled compound as gum. Yield 8.64 g.

Provenance & Evidence