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

HRID 2176988Notes

Reaction equation

HRID 2176988 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-e9be1ecc317c46818765fbf7792412c7
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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