Hydrochloric Acid → beta-Chlorocinnamoyl chloride

HRID 2107899Notes

Reaction equation

HRID 2107899 reaction equation
CC[O:3][C:4]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:16].[ClH:21].P(Cl)(Cl)(Cl)=O>P(Cl)(Cl)Cl>[Cl:21][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:6][C:4]([Cl:16])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachloride

Product 1

HCID 54043414beta-Chlorocinnamoyl chlorideYield 86%

Reagents, catalysts & solvents 1

HCID 24387Phosphorus trichlorideSolvent2×

Procedure

A solution of 60 g (0.312 mol) ethyl benzoyl acetate in 96 ml (150 g) of phosphorous trichloride is added dropwise to 150 g (0.72 mol) of phosphorous pentachloride under nitrogen. The suspension that forms is cautiously brought to reflux temperature (HCl evolution observed) and is refluxed and stirred for 2-21/2 hrs. The solution that forms is stripped of phosphorous trichloride and phosphorous oxychloride at atmospheric pressure (76°-82° C.). The pot residue is distilled at 97°-108° C./0.75 mm to give 54 g (86% yield) of product as an isomeric mixture.

Workup

  1. temperatureis refluxed
  2. distillationThe pot residue is distilled at 97°-108° C./0.75 mm

Sources & evidence

ORD record
ord-aa4ccba3a19345139816e437cd49b084
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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