2-Methyl-2-butene → 4-Benzyloxy-3,5-dimethylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

2-Methyl-2-butene (3.31 mL, 31.2 mmol) and sodium chlorite (282 mg, 3.12 mmol) were sequentially added to a mixture of 4-(benzyloxy)-3,5-dimethyl-benzaldehyde (455 μl, 2.081 mmol) and potassium dihydrogen phosphate (425 mg, 3.12 mmol) in 1:1 water/t-BuOH (8.0 mL), and the resulting mixture was stirred at 25° C. for 4 h. Additional potassium dihydrogen phosphate (991 mg, 7.28 mmol) and sodium chlorite (659 mg, 7.28 mmol) were then sequentially added, and the resulting mixture was stirred at 25° C. for 15 h. The reaction mixture was subsequently partitioned between EtOAc (120 mL) and 0.02N aq. HCl (50 mL). The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes) gave 4-(benzyloxy)-3,5-dimethylbenzoic acid as a white solid. MS (ESI) m/z: Calculated: 256.1; Observed: 257.2 (M++1).

Provenance & Evidence