2'-Nitroacetophenone → 1-(2-Nitrophenyl)ethanol

HRID 1811379Notes

Reaction equation

HRID 1811379 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13])([O-:5])=[O:4]>CO.O1CCOCC1.C(OCC)(=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([OH:14])[CH3:13])([O-:5])=[O:4]

Participants

6

Reactant 2

HCID 113462'-NitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 978511-(2-Nitrophenyl)ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

NaBH4 (3.24 g, 85.60 mmol) was slowly added to a solution of 2′-nitroacetophenone NAP (3.74 g, 22.65 mmol) in a mixture of methanol (34 mL) and dioxane (22 mL). The reaction mixture was stirred at room temperature for one hour and then diluted with ethyl acetate (100 mL) and washed with water (25 mL). The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo to yield 1-(2-nitrophenyl)ethanol dC.13a (3.49 g, 92%) as a white powder.

Workup

  1. washwashed with water (25 mL)
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63a484d75d32415c99ca65796749e611
Source dataset
uspto-grants-2013_01
Patent number
US08361727B2

Reaction notes

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