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 2 N 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 (19.2 g) as a pale yellow solid; LC-MS: tR=1.00 min; 1H NMR (D6-DMSO): δ1.13-1.22 (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 (s br, 1H).

Provenance & Evidence