Water → 3'-Chloro-4'-methoxyacetophenone

HRID 1860582Notes

Reaction equation

HRID 1860582 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].[C:12]([O-])([O-])=O.[K+].[K+].[OH-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 10515141-(3-Chloro-4-hydroxyphenyl)ethanone

Product 1

HCID 5208573'-Chloro-4'-methoxyacetophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(3-chloro-4-hydroxylphenyl)ethanone (1.7 g, 10 mmol) in DMF was added K2CO3 (1.52 g, 11 mmol), 2 N NaOH solution (5 ml), and Mel (0.68 ml). The reaction mixture was stirred at room temperature for 2 hours. Another 1.24 ml of Mel was added, and the reaction mixture was stirred for an additional 30 minutes. Water (50 ml) was added, and the product was extracted with 200 ml of EtOAc and 100 ml of benzene. The organic layer was washed with brine (50 ml), and dried with MgSO4, and the solvent was removed in vacuo to give the title compound in quantitative yield.

Workup

  1. additionAnother 1.24 ml of Mel was added
  2. stirringthe reaction mixture was stirred for an additional 30 minutes
  3. extractionthe product was extracted with 200 ml of EtOAc and 100 ml of benzene
  4. washThe organic layer was washed with brine (50 ml)
  5. dry with materialdried with MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-693184de283446d99aa69eed4a23cde3
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

Loading…