Hydrochloric Acid → beta-Chlorocinnamoyl chloride

HRID 1089054Notes

Reaction equation

HRID 1089054 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./0.75mm 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./0.75mm

Sources & evidence

ORD record
ord-f4f4670f56214e268cfebad9975c00f4
Source dataset
uspto-grants-1990_10
Patent number
US04964896

Reaction notes

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