Ammonium Chloride → alpha-Methyl-4-(trifluoromethoxy)benzenemethanol

Participants

Reaction Steps

Methyl magnesium iodide [prepared from magnesium (3.5 g) and methyl iodide (20.5 g)] in diethyl ether (50 ml) was treated with a solution of 4-trifluoromethoxybenzaldehyde [20 g, described by Yagupolskii and Troitskaya, Zhur. Obschii Khim., 30, 3129 (1960)] in diethyl ether (25 ml) at reflux with stirring. After the addition the mixture was heated at reflux for 6 hours. The cooled solution was treated with a solution of ammonium chloride (35 g) in water (100 ml) at 0°-5° C. The organic layer was separated and the aqueous layer was washed with diethyl ether (3×50 ml). The ether solution and washings were combined, washed with water (2×100 ml), dried over sodium sulphate and evaporated to dryness. (+)-1-(4-Trifluoromethoxyphenyl)ethanol (20.3 g) was obtained as a clear colourless oil of sufficient purity for subsequent reaction.

Provenance & Evidence