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

HRID 1667299Notes

Reaction equation

HRID 1667299 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH:6]=[O:7]>CO>[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 124670502-Chloro-6-methylbenzaldehyde

Product 1

HCID 20579023(2-Chloro-6-methylphenyl)methanolYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under ice cooling, 185 mg of sodium borohydride was added to a solution of 1.51 g of 2-chloro-6-methylbenzaldehyde in 15 ml of methanol, followed by stirring for 35 minutes. The reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride was added to the residue. The mixture was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 1.24 g of 2-chloro-6-methylbenzyl alcohol as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-da8e655f95b642eaad8f11ecb96a2fbe
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

Loading…