Toluene → 3-(2,6-Dichlorophenyl)propan-1-ol

A solution of 3-(2,6-dichlorophenyl)propanoic acid (5.00 g, 22.8 mmol) in THF (114 mL) was stirred at room temperature as triethylamine (3.2 mL, 22.8 mmol) was added. The solution was then cooled in an ice/water bath before the addition of a 1 M solution of isopropylchloroformate in toluene (22.8 mL, 22.8 mmol). After 30 minutes the mixture was filtered into a mixture of sodium borohydride (1.13 g, 30 mmol) in water (8 mL). The resulting mixture was stirred in an ice/water bath and allowed to warm slowly to room temperature. The mixture was allowed to stir at room temperature overnight, then was filtered. The filtrate was partitioned between brine and ethyl acetate. The organic layer was dried with MgSO4, filtered, and concentrated. The residue was purified by chromatography (silica gel, 3:7 ethyl acetate:hexanes) to provide the title compound (3.85 g, 77% as •0.17 EtOAc). 1H NMR (d6-DMSO): δ 7.41 (d, J=8 Hz, 2H), 7.22 (t, J=8 Hz, 1H), 4.57 (t, J=5 Hz, 1H), 3.48-3.43 (m, 2H), 2.88-2.84 (m, 2H), 1.65-1.58 (m, 2H).

1. additionwas added
2. stirringto stir at room temperature overnight
3. filtrationwas filtered
4. customThe filtrate was partitioned between brine and ethyl acetate
5. dry with materialThe organic layer was dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by chromatography (silica gel, 3:7 ethyl acetate:hexanes)

ORD record

ord-279790afecd7430fa0fe28575b3a043d

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705028B2