Acetic Anhydride → 4-Acetamido-3-methoxybenzyl alcohol

HRID 1604588Notes

Reaction equation

HRID 1604588 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11].[C:12](OC(=O)C)(=[O:14])[CH3:13]>CO>[C:12]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53420748(4-Amino-3-methoxyphenyl)methanol

Product 1

HCID 538917484-Acetamido-3-methoxybenzyl alcoholYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-3-methoxybenzyl alcohol (900 mg) in methanol was added acetic anhydride (1.8 g) under ice cooling, and the mixture was stirred for 1 hour at the same temperature. After evaporation, the residue was dissolved in ethyl acetate, and the solution was washed with sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated in vacuo to give 4-acetamido-3-methoxybenzyl alcohol (840 mg) as solid.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with sodium bicarbonate solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa901595b69a4303a7e4603410e9a176
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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