Sodium borohydride → (2-Chloro-6-methylphenyl)methanol

HRID 1679894Notes

Reaction equation

HRID 1679894 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 124670502-Chloro-6-methylbenzaldehyde

Product 1

HCID 20579023(2-Chloro-6-methylphenyl)methanolYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 24 g of 2-chloro-6-methylbenzaldehyde [L. G. Humber, J. Med. Chem., 7, 826 (1964)] in 200 ml of methanol is cooled in an ice bath while 6.0 g of sodium borohydride is added in portions. After stirring overnight at room temperature, the mixture is concentrated to dryness and the residue is partitioned between water and ether. The organic layer is washed with dilute hydrochloric acid, dried, and concentrated to yield the crude product. Recrystallization from benzene/hexane gives 20.8 g of 2-chloro-6-methylbenzyl alcohol, mp 83°-86° C. in two crops.

Workup

  1. additionis added in portions
  2. concentrationthe mixture is concentrated to dryness
  3. customthe residue is partitioned between water and ether
  4. washThe organic layer is washed with dilute hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customto yield the crude product
  8. customRecrystallization from benzene/hexane

Sources & evidence

ORD record
ord-a87ba4c33ad2409c91c402c909378b6b
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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