Benzenepropanoic acid → Benzenepropanoyl chloride

HRID 556028Notes

Reaction equation

HRID 556028 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:14])=O.[Cl-].[Ca+2].[Cl-]>>[C:1]1([CH2:7][CH2:8][C:9]([Cl:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 24386Thionyl ChlorideHCID 5284359Calcium Chloride

Product 1

HCID 64801Benzenepropanoyl chloride

Procedure

To a 100 ml eggplant-shaped flask were added 20.0 g (133.2 mmol) 3-phenylpropionic acid and 24.5 g (205.9 mmol) thionyl chloride, a reflux condenser pipe carrying a calcium chloride drying pipe and a sodium hydroxide acidic gas absorption device was mounted, the mixture was refluxed for 1 hour under magnetic agitation, distilled under reduced pressure to remove excessive thionyl chloride to give crude 3-phenylpropionyl chloride as a pale yellow oil, which was directly used in the reaction of following step without purification.

Workup

  1. customa sodium hydroxide acidic gas absorption device
  2. temperaturethe mixture was refluxed for 1 hour under magnetic agitation
  3. distillationdistilled under reduced pressure
  4. customto remove excessive thionyl chloride

Sources & evidence

ORD record
ord-c4232b2fbcd64e419ca5559364bc96e9
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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