Acetyl chloride → Phenyl acetate

HRID 329315

Reaction equation

HRID 329315 reaction equation
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:10])[CH3:9]>CCOCC>[C:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 119047Phenolate

Product 1

HCID 31229Phenyl acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A vigorously stirred suspension of thallous phenoxide (5 g., 0.017 m.) in anhydrous ether (15 ml.) is treated dropwise with freshly distilled acetyl chloride (1.33 g., 0.017 m.) in anhydrous ether (3 ml.) over 5 mins. at such a rate that the exothermic reaction is controlled. The mixture is then stirred for 1 hour at room temperature, the precipitated thallous chloride removed by filtration through Celite and the solvent evaporated under vacuum. The residual colorless oil is distilled to give phenyl acetate, 2.27 g., 98%, b.p. 110°/58 mm.

Workup

  1. customat such a rate that the exothermic reaction
  2. customthe precipitated thallous chloride
  3. customremoved by filtration through Celite
  4. customthe solvent evaporated under vacuum
  5. distillationThe residual colorless oil is distilled

Sources & evidence

ORD record
ord-d43d63ba1dfa446897033aa7e503357e
Source dataset
uspto-grants-1977_04
Patent number
US04020073

Linked notes

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