Ammonium Chloride → 1-(3,5-Dimethoxyphenyl)ethanol

HRID 1364408Notes

Reaction equation

HRID 1364408 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 116799221-(3,5-Dimethoxyphenyl)ethanolYield 111.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dimethoxyacetophenone (1 g; 5.5 mmol) in methanol (30 mL) is added sodium borohydride (315 mg; 8.3 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 1.12 grams of 1-(3,5-dimethoxyphenyl)-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-d89eed1d149e48f8a42b65a2e12db915
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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