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

HRID 516858Notes

Reaction equation

HRID 516858 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+]>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 124670502-Chloro-6-methylbenzaldehyde

Product 1

HCID 20579023(2-Chloro-6-methylphenyl)methanol

Procedure

To a stirred solution of 2-chloro-6-methylbenzaldehyde (6.11 g, 39.5 mmol) in THF(2): methanol(3) (30 ml) was added in portion NaBH4 (2.24 g, 59.28 mmol) at 0° C. under argon. The reaction mixture was stirred at the same temperature for 1.3 hours and then quenched with cold sat. NH4Cl solution, extracted with EtOAc, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate, 2:1) to give the title compound.

Workup

  1. customquenched with cold sat. NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-8cc9046198b4494898fe96ddf0fff659
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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