Sodium borohydride → 2-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol

HRID 1740321Notes

Reaction equation

HRID 1740321 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:9]=2[CH:10]=[O:11])=[CH:4][C:3]=1[CH3:18].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:9]=2[CH2:10][OH:11])=[CH:4][C:3]=1[CH3:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 133169792-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzaldehyde

Product 1

HCID 133169802-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcoholYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.90 grams (12 mmol) of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzaldehyde (prepared according to Stokker, Jour. Med. Chem. Vol. 29 p.170, 1986) was reduced with 0.454 grams (12 mmol) of sodium borohydride in ethanol (20 mL) at 0° C. The reaction was stirred 1 hr, quenched with aqueous ammonium chloride and the mixture extracted with ether. The organic portion was dried (MgSO4) and concentrated to give 2.90 grams of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol as an oil which solidified on standing. The crude solid was treated with 1.31 mL of thionyl chloride and heated on a steam bath for 1 hour. After cooling to room temperature, the crude mixture was taken up in water and extracted with ether. The ether was washed with water and dried(MgSO4), and concentrated to give an oily residue which was purified by silica gel chromatography (25% methylene chloride/75% hexane) to give 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl chloride as a solid.

Workup

  1. customquenched with aqueous ammonium chloride
  2. extractionthe mixture extracted with ether
  3. dry with materialThe organic portion was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-616b6b9a01ae427582ec12da0999c8ed
Source dataset
uspto-grants-1999_10
Patent number
US05969017

Reaction notes

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