Water → (1-Phenyl-2-naphthyl)methanol

Participants

Reaction Steps

A 1.0M solution of lithium aluminiumhydride in THF (10 ml, 10 mmol) was placed under an atmosphere of nitrogen and a solution of 1-phenyl-2-naphthalenecarboxylic acid (2.4 g, 10 mmol, Synthesis 1983, 105) in dry THF (10 ml) was added dropwise. When addition was complete the mixture was stirred for 30 minutes at ambient temperature and then 30 minutes at reflux. The reaction mixture was allowed to cool and carefully water (0.4 ml), 4N sodium hydroxide (0.4 ml) and water (1.2 ml) were added successively. The mixture was stirred at ambient temperature for 30 minutes, diluted with diethylether and filtered. The solvent was evaporated in vacuo and the residue was dissolved in toluene. After drying (MgSO4) the solvent was evaporated in vacuo to give 2.3 g of crude (1-phenyl-2-naphthyl)methanol.

Provenance & Evidence