Water → 4-Phenyl-2-butanol

Temperature

0 °C

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+).

1. temperatureto warm to room temperature overnight
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ether (2×25 mL)
4. concentrationconcentrated
5. additionThe resulting aqueous residue was poured into ether (50 mL)
6. customThe organic layer was removed
7. dry with materialdried (MgSO4)
8. concentrationconcentrated

ORD record

ord-fcab4a9c6d844443923cd733cfef1d65

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05312950