Acetic Anhydride → 3-Acetaminobenzyl alcohol

HRID 38157

Reaction equation

HRID 38157 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1COCC1.CCOC(C)=O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 802933-Aminobenzyl alcohol

Product 1

HCID 966393-Acetaminobenzyl alcoholYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled suspension of 3-aminobenzyl alcohol (9.24 g, 75 mmol) in THF (50 mL) was added neat acetic anhydride (8.1 mL, 86 mmol). The reaction mixture was stirred cold for 1 hr, diluted with EtOAc, washed with aq. NaOH and brine, and concentrated in vacuo to give N-[3-(hydroxymethyl)phenyl]acetamide (10.5 g, 85%).

Workup

  1. washwashed with aq. NaOH and brine
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cda3a113e7984ffbbcb9d5012335d664
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Linked notes

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