Acetyl chloride → Phenyl acetate

HRID 268510

Reaction equation

HRID 268510 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-52748cb56aef414f9320e2f419e3bd4b
Source dataset
uspto-grants-1976_03
Patent number
US03947488

Linked notes

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