Potassium Permanganate → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (25.0 g, 98.3 mmol) in acetone (500 mL), KMnO4 (20.2 g, 127.8 mmol) is added. The mixture becomes warm (45° C.). The mixture is stirred at rt for 16 h before it is filtered over glass filters. The clear, colourless filtrate is concentrated, diluted with water and acidified with 2N aq. HCl, then extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 4-benzyloxy-3-ethyl-5-methyl-benzoic acid as a pale yellow solid (19.2 g). LC-MS: tR=1.00 min; 1H NMR (D6-DMSO): δ 1.13-1.22 (m, 3H), 2.32 (s, 3H), 2.64-2.72 (m, 2H), 4.87 (s, 2H), 7.34-7.56 (m, 5H), 7.69 (m, 2H), 12.66 (br s, 1H).

Provenance & Evidence