Acetic Anhydride → 4-Acetamido-3-methoxybenzyl alcohol

HRID 2287598Notes

Reaction equation

HRID 2287598 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-05f84ca2f839457eab68056234964eb6
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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