Sodium borohydride → 2,alpha-Dimethyl-3-nitrobenzenemethanol

HRID 2051233Notes

Reaction equation

HRID 2051233 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH3:14]>CO.O>[CH3:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]([CH3:14])[OH:15]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 126307991-(2-Methyl-3-nitrophenyl)ethanone

Product 1

HCID 151328672,alpha-Dimethyl-3-nitrobenzenemethanolYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (0.02 g, 0.6 mmol) is added to a solution of 1-(2-methyl-3-nitrophenyl)ethanone (0.2 g, 1.1 mmol) in methanol (50 mL) at 0° C. The reaction mixture is stirred at room temperature for 1.5 hours, and then is diluted with water (100 mL). The aqueous mixture is stirred at room temperature an additional 5 hours followed by extraction with ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, and evaporated. Flash chromatography of the residue (silica, methylene chloride) gives 2,α-dimethyl-3-nitrobenzenemethanol (0.14 g, 77%) as an oil.

Workup

  1. stirringThe aqueous mixture is stirred at room temperature an additional 5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-208960fa1c4e4484bc3754e36adbee2b
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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