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

HRID 2176987

Reaction equation

HRID 2176987 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-f34503721ede4d6d87a5b746acb3f354
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Linked notes

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