methyl 2-hydroxy-5-(hydroxymethyl)benzoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl-5-formylsalicylate (Kadaba, J. Pharm. Sci. 1974, 63, 1333-1335) (1.80 g, 0.01 mol) in methanol (20 mi) at 0° C. was added sodium borohydride (0.38 g, 0.01 mol) in 4 portions during 0.5 h. The solution was further stirred at 0° C. for 2 h and then at room temperature for 0.3 h. It was neutralized with hydrochloric acid and concentrated under vacuum. The residue was passed through a column of silica gel using 1:1 ethyl acetate:hexane as the eluent to give 1.0 g (55%) of methyl-2-hydroxy-5-hydroxymethylbenzoate as a pale yellow powder, mp 66°-67° C. at room temperature for 0.3 h concentrated under vacuum