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

HRID 1772199Notes

Reaction equation

HRID 1772199 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.O=S(Cl)[Cl:14]>>[C:1]([Cl:14])(=[O:11])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 87842-Propenoic acid, 3-phenyl-HCID 24386Thionyl Chloride

Product 1

HCID 660233-Phenylprop-2-enoyl chloride

Procedure

Cinnamic acid (25 g, 168.74 mmol) was treated with SOCl2 (150 ml) for 2 hours at 70° C. in a round-bottomed flask. The volatiles were distilled out under vacuum to afford cinnamoyl chloride as a yellow oil (25.2 g, crude), which was used in the next step without further purification.

Workup

  1. distillationThe volatiles were distilled out under vacuum

Sources & evidence

ORD record
ord-1ccd6a242fb34c7dab61a725dbd1c561
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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