Acetonitrile → 2-Hydroxy-1-(4-methoxyphenyl)ethanone

Participants

Reaction Steps

4-Methoxyacetophenone (10 g; 66.59 mmol) was added to a solution of acetonitrile (350 ml), water (70 ml) and trifluoroacetic acid (TFA) (10.26 ml; 133.20 mmol). Then (bis(trifluoroacetoxy)iodo)benzene was added, and the reaction mixture was heated under reflux for 3 h. The acetonitrile was then stripped off in a rotary evaporator, and the reaction mixture was partitioned in NaHCO3 solution/CH2Cl2. After extraction with CH2Cl2 (2×), the combined organic phases were dried over MgSO4, and the solvent was removed in a rotary evaporator. Purification by column chromatography (CH2Cl2/MeOH 50:1) resulted in 2-hydroxy-1-(4-methoxyphenyl)ethanone (6.0 g; 36.1 mmol). MS: 167.15 (M+H); Rt: 0.83 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Provenance & Evidence