Sodium Hydroxide → 3-Benzylbenzyl alcohol

Participants

Reaction Steps

To a suspension of 3-benzylbenzoic acid (15 g, 70 mmol) in THF (100 ml) a solution of lithium aluminiumhydride in THF (80 ml, 80 mmol, 1M) was added dropwise. When addition was complete the mixture was stirred for 30 minutes at ambient temperature and then heated at reflux for 40 minutes. The reaction mixture was allowed to cool and water (3 ml), diethyl ether (100 ml), 4N sodium hydroxide (6 ml) and water (12 ml) were added successively. The mixture was stirred for 30 minutes, filtered and the solvent evaporated in vacuo. The residue was dissolved in toluene (200 ml) and dried (MgSO4) overnight. The solvent was evaporated in vacuo to give 11.9 g of crude 3-benzylbenzylalcohol as an oil.

Provenance & Evidence