Water → 1-Phenoxy-2-propanol

Temperature

0 °C

Phenoxy-2-propanone (3.4 mL, 25 mmol) was dissolved in ethanol (30 mL) and cooled to 0° C. Sodium borohydride (0.95 g; 25 mmol; 1 equiv.) was added. The mixture was stirred and allowed to warm to room temperature overnight. All of the starting material was gone according to tlc analysis, so the mixture was poured into water (30 mL) and ether (30 mL). The layers were separated and the aqueous layer was extracted with ether (2×20 mL). The organic layers were combined and concentrated. The resulting aqueous residue was poured into ether (25 mL). The organic layer was removed, dried (MgSO4), and concentrated to provide 1e (3.2 g; 85%). 1H nmr (300 MHz, CDCl3): 7.332-7.261 (3H, m); 6.995-6.904 (2H, m); 4.15-4.24 (1H, m); 3.972-3.768 (2H, m); 1.559 (1H, s); 1.290 (3H, d, J=6.38 Hz). IR (neat film, cm-1): 3350 (b, s); 2900 (s); 1590 (m). EIMS (m/e): 152 (M+).

1. temperatureto warm to room temperature overnight
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ether (2×20 mL)
4. concentrationconcentrated
5. additionThe resulting aqueous residue was poured into ether (25 mL)
6. customThe organic layer was removed
7. dry with materialdried (MgSO4)
8. concentrationconcentrated

ORD record

ord-a92c87fe015d4d3ba7d770b991676f8e

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05312950