N-(4-Methoxyphenyl)Acetamide → N-(3-Acetyl-4-hydroxyphenyl)acetamide

HRID 1819553Notes

Reaction equation

HRID 1819553 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[C:13]([C:4]1[CH:5]=[C:6]([NH:9][C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][C:3]=1[OH:2])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 5827N-(4-Methoxyphenyl)AcetamideHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 81720N-(3-Acetyl-4-hydroxyphenyl)acetamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of N-(4-methoxy-phenyl)-acetamide (5.253 g, 32 mmol) and acetyl chloride (6.6 ml, 93 mmol, 2.9 equ) in dichloromethane (55 ml) was added aluminium trichloride (14.55 g, 109 mmol, 3.4 equ) in portions over 90 minutes. The reaction was then heated to reflux for 4.5 hours and cooled overnight. The mixture was poured onto ice then extracted into dichloromethane (5×), dried (MgSO4) and concentrated in vacuo to give N-(3-acetyl-4-hydroxy-phenyl)-acetamide (5.336 g, 87%) as a pale green solid.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 4.5 hours
  3. temperaturecooled overnight
  4. additionThe mixture was poured onto ice
  5. extractionthen extracted into dichloromethane (5×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70cd97b56c2e45c7bc6190bf51680b57
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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