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

HRID 323569Notes

Reaction equation

HRID 323569 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-a9995bf33c194be0b7c0d5906660396a
Source dataset
uspto-grants-2001_04
Patent number
US06214810B1

Reaction notes

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