Potassium Acetate → 2-Benzyloxy-4-formylbenzoic acid

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Reaction Steps

A mixture of 3-benzyloxy-4-trifluoromethanesulfonylbenzaldehyde (350 mg, 0.97 mmol, 1 eq), potassium acetate (380 mg, 3.89 mmol, 4 eq), palladium (II) diacetate (32 mg, 0.05 mmol, 0.05 eq) and 1,1′-bis-(diphenylphosphino)ferrocene (dppf) (108 mg, 0.19 mmol, 0.2 eq) in anhydrous dimethylsulfoxide (6 mL) was purged with carbon monoxide and stirred for 5 min. The reaction mixture was then heated to 60□C. and stirred under a carbon monoxide balloon for 3 h. The solution was allowed to cool to room temperature, and acidified to pH 1 with 10% HCl and then extracted with ethyl acetate (2×20 mL). The organic extracts were combined and washed with brine, then extracted with saturated aqueous sodium bicarbonate (3×20 mL). The aqueous extracts were combined, washed with ethyl acetate (2×20 mL), acidified to pH 1 with 10% HCl and back extracted with ethyl acetate (2×20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a cream coloured powder (146 mg, 59%). 1H NMR (CDCl3) δ10.08 (s, 1H, O═C—H), 5.39 (s, 2H, OCH2Ph).

Provenance & Evidence