3-Methoxyacetophenone → (+-)-1-(3-Methoxyphenyl)ethanol

HRID 1364407

Reaction equation

HRID 1364407 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)=[O:3].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 114603-MethoxyacetophenoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride

Product 1

HCID 90902(+-)-1-(3-Methoxyphenyl)ethanolYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-methoxyacetophenone (3 g; 20 mmol) in methanol (60 mL) is added sodium borohydride (1.13 g; 30 mmol) in four portions over one hour. The reaction is stirred at room temperature overnight, neutralized with saturated ammonium chloride, and extracted with ethyl acetate. The organics are separated, washed with water, and dried over magnesium sulfate. The solvent is removed to give 2.62 grams of 1-(3-methoxyphenyl)-ethanol.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organics are separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-349df5ab7597479883ecf1d6154bd7e0
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Linked notes

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