m-Nitroacetophenone → alpha-Methyl-3-nitrobenzenemethanol

HRID 1903417Notes

Reaction equation

HRID 1903417 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([OH:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 8494m-NitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 223135alpha-Methyl-3-nitrobenzenemethanolYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of sodium borohydride (0.4 g, 10 mmol) in ethanol (10 ml) was treated with m-nitroacetophenone (3.3 g, 20 mmol) at 20° C. for 20 mins. The solution was the diluted with aqueous potassium carbonate and extracted with chloroform. The extracts were dried (magnesium sulphate) and evaporated in vacuo to give 1-(m-nitrophenyl)ethanol as an oil (2.9 g, 90%);

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extracts were dried (magnesium sulphate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-64a0de1e16644c6c8d164d9090634157
Source dataset
uspto-grants-1984_03
Patent number
US04436751

Reaction notes

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