m-Nitroacetophenone → alpha-Methyl-3-nitrobenzenemethanol

HRID 655313

Reaction equation

HRID 655313 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO.ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([OH:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 8494m-NitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 223135alpha-Methyl-3-nitrobenzenemethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

26.4 g (160 mmol) of 1-(3-nitrophenyl)ethanone are suspended in 270 ml of methanol, and 6.1 g (160 mmol) of sodium borohydride are added in portions with ice cooling. The reaction mixture is subsequently stirred for a further 3 h without cooling, diluted with 300 ml of dichloromethane and washed with 3×200 ml of water. The organic phase is dried over sodium sulfate and evaporated to dryness.

Workup

  1. temperaturewithout cooling
  2. washwashed with 3×200 ml of water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-68cae19d5e03440abae9b8c78f7b0c6c
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Linked notes

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