4-Chloro-3-methylphenol → 4-Chloro-3-methylphenyl acetate

HRID 47151

Reaction equation

HRID 47151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>S(=O)(=O)(O)O.O>[C:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:9])[CH:4]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 17324-Chloro-3-methylphenolHCID 7918Acetic Anhydride

Product 1

HCID 5215554-Chloro-3-methylphenyl acetate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

43.0 g (0.30 mol) of 4-chloro-3-methylphenol, 34 ml (0.36 mol) of acetic anhydride and a few drops of concentrated sulfuric acid were stirred for 2 h at 60° C. in a 250 ml flask equipped with a reflux condenser. The reaction mixture was cooled to room temperature, poured into 200 ml of water and stirred for 1 h at room temperature. The mixture was then extracted with 400 ml of diethyl ether. The organic phase was dried over magnesium sulfate and the ether was distilled off. The raw product is subsequently distilled under reduced pressure (b.p. 65-68° C., 20 mbar).

Workup

  1. customequipped with a reflux condenser
  2. extractionThe mixture was then extracted with 400 ml of diethyl ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. distillationthe ether was distilled off
  5. distillationThe raw product is subsequently distilled under reduced pressure (b.p. 65-68° C., 20 mbar)

Sources & evidence

ORD record
ord-2abe76b980254f9eb3d2fd29f5a44d81
Source dataset
uspto-grants-2004_03
Patent number
US06699405B2

Linked notes

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