Methanol → 1,3,5-Benzenetrimethanol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of trimethyl 1,3,5-benzenetricarboxylate (10.45 g, 41.4 mmol) in 70 ml of anhydrous THF is added at room temperature a 10M solution of borane-methyl sulfide complex (25 ml, 248 mmol) and the solution is heated to reflux for 3 h. The mixture is then added slowly to 50 ml of MeOH and the resulting mixture is heated at 70° C. for 10 min to remove the methyl sulfide. Evaporation of solvent, washing twice with 50 ml of MeOH and evaporation of MeOH gives 1,3,5-tris(hydroxymethyl)benzene (6.96 g, 100%). 1H NMR (D2O): δ 4.52 (6H, s), 7.15 (3H, s).

Provenance & Evidence