4-Chlorophenol → 4-Chlorophenyl Acetate

HRID 1582615Notes

Reaction equation

HRID 1582615 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[Cl:8][C:9]1[CH:14]=CC(O)=[CH:11][CH:10]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[C:5]([O:4][C:1]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:2]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 46844-Chlorophenol2×HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 134104-Chlorophenyl AcetateYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Acetic anhydride (80.1 g, 0.78 mol) and one drop of concentrated sulfuric acid were added to 4-chlorophenol [compound (6-1)] (100 g, 0.78 mol) at room temperature, and the mixture was stirred for 17 hours. The resultant mixture was added to ice-water, and converted to alkaline by the addition of sodium hydroxide (20% aqueous solution), followed by extraction with diethyl ether. The organic layer was washed with water, dried over magnesium sulfate. Subsequently, the solvent was removed under reduced pressure, and then the residue was subjected to distillation under reduced pressure (81° C./1.5 mmHg), to thereby yield 4-chlorophenyl acetate as a colorless oily product (130 g, yield: 98.0%).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customSubsequently, the solvent was removed under reduced pressure
  5. distillationthe residue was subjected to distillation under reduced pressure (81° C./1.5 mmHg)

Sources & evidence

ORD record
ord-e763dffd677b4489a12e5d375c2b09b8
Source dataset
uspto-grants-2004_05
Patent number
US06737434B2

Reaction notes

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