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

HRID 465862

Reaction equation

HRID 465862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.B.O1CCCC1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 123137beta-(p-Chlorophenyl)propionic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 2219714-ChlorobenzenepropanolYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-94e509240ef649b7855094cdaca12e72
Source dataset
uspto-grants-1992_10
Patent number
US05153327

Linked notes

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