beta-(p-Chlorophenyl)propionic acid → 4-Chlorobenzenepropanol

To a stirred solution of 5.0 g (27 mmol) of 3-(4-chlorophenyl)propionic acid in 30 ml of tetrahydrofuran at 0° C., 30 ml (1M in THF, 30 mmol) of borane-tetrahydrofuran solution was added dropwise. The reaction was stirred for 15 hours. The reaction mixture was concentrated in vacuo. The residue was quenched with water and partitioned between diethyl ether and saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted twice with 40 ml of diethyl ether. The organic layers were combined and washed with brine, dried over MgSO4 and concentrated in vacuo to obtain 3.9 g of a colorless oil.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customThe residue was quenched with water
3. custompartitioned between diethyl ether and saturated sodium bicarbonate
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted twice with 40 ml of diethyl ether
6. washwashed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-fab93a307b2a4cc1848b3d1265a8102e

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05100889