Water → 4-Phenyl-2-butanol

Participants

Reaction Conditions

Reaction Steps

Benzylacetone (7.5 mL, 50 mmol) was dissolved in ethanol (50 mL) and cooled to 0° C. Sodium borohydride (1.89 g, 50 mmol, 1 equiv.) was added. The mixture was stirred and allowed to warm to room temperature overnight. All of the starting material was gone by tlc analysis, so the mixture was poured into water (50 mL) and ether (50 mL). The layers were separated and the aqueous layer was extracted with ether (2×25 mL). The organic layers were combined and concentrated. The resulting aqueous residue was poured into ether (50 mL). The organic layer was removed, dried (MgSO4), and concentrated to provide 1c (6.86 g; 91%). 1H nmr (300 MHz, CDCl3): 7.38-7.15 (5H, m); 3.85 (1H, m(6), J=6.17 Hz); 2.82-2.61 (2H, m); 1.79 (2H, q, J=7.12 Hz); 1.421 (1H, s); 1.236 (3H, d, J=6.09 Hz). IR (neat film, cm-1): 3250 (b); 2900 (b). EIMS (m/e): 150 (M+).

Provenance & Evidence