Benzoyl chloride → Allyl benzoate

HRID 65133

Reaction equation

HRID 65133 reaction equation
C(Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](=[O:19])([O:15][CH2:16][CH:17]=[CH2:18])OCC=C>[Cl-].[Zn+2].[Cl-]>[C:10]([O:15][CH2:16][CH:17]=[CH2:18])(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 84764Carbonic acid, di-2-propen-1-yl ester

Product 1

HCID 11406Allyl benzoateYield 82%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
60 °C

Procedure

In a glass reactor benzoyl chloride (7.03 g, 0.05 mole), diallyl carbonate (7.1 g, 0.05 mole) and zinc chloride (0.136 g, 0.001 mole) were combined. The reacinitiated at room temperature. After heating at 60° C. for 3 hours and heating at 80° C. for an additional 3 hours, the reaction was discontinued. Distillation gave 6.65 g (78 percent yield) of allyl benzoate which was identified by nuclear magnetic resonance spectroscopy.

Workup

  1. customreacinitiated at room temperature
  2. temperatureheating at 80° C. for an additional 3 hours
  3. distillationDistillation

Sources & evidence

ORD record
ord-39ac0fe3490b4b4ca1802b534a76f6ac
Source dataset
uspto-grants-1986_09
Patent number
US04612386

Linked notes

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