2-Propenoic acid, 3-phenyl- → 3-Phenylprop-2-enoyl chloride

HRID 1274035Notes

Reaction equation

HRID 1274035 reaction equation
[C:1]([OH:11])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Al].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[C:1]([Cl:15])(=[O:11])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 87842-Propenoic acid, 3-phenyl-HCID 24386Thionyl ChlorideHCID 5359268Aluminum

Product 1

HCID 660233-Phenylprop-2-enoyl chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 mmol of the cinnamic acid (4) was solved in anhydrous benzene and stirred in an aluminum foil covered flask. 3 mmol thionyl chloride was added and refluxed under stirring overnight. The solvent was removed under vacuum and the product (5) recrystallized from hexane. The derivatives of cinnamoyl chloride were obtained in a 90% yield.

Workup

  1. temperaturerefluxed
  2. customThe solvent was removed under vacuum
  3. customthe product (5) recrystallized from hexane

Sources & evidence

ORD record
ord-d6d6da01f7d04df99a3fe94f1af306d3
Source dataset
uspto-grants-2000_12
Patent number
US06156232

Reaction notes

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