Thionyl Chloride → 1-Phenyl-2-chloro-cyclohex-3-ene-carboxylic-acid-ethyl-ester

HRID 460770Notes

Reaction equation

HRID 460770 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][CH:9]=[CH:8][CH:7]1O)=[O:5])[CH3:2].S(Cl)([Cl:21])=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][CH:9]=[CH:8][CH:7]1[Cl:21])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 213945801-Phenyl-2-hydroxy-cyclohex-3-ene-1-carboxylic-acid-ethyl-ester

Product 1

HCID 213945601-Phenyl-2-chloro-cyclohex-3-ene-carboxylic-acid-ethyl-ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15 g of 1-phenyl-2-hydroxy-cyclohex-3-ene-1-carboxylic-acid-ethyl-ester and 15 cc. of thionyl chloride and 1 cc. of dimethylformamide are heated under reflux for 10 minutes. Then direct distillation is done. 12.2 g of 1-phenyl-2-chloro-cyclohex-3-ene-1-carboxylic-acid-ethyl-ester of the boiling point 0.1/122°-5° C are obtained. By reacting with 12 g of β-phenylethyl amine in 100 cc. of DMSO for 2 hrs. at 100° C, processing as described above, 6.0 g of hydrochloride m.p. 179°-82° C are obtained.

Workup

  1. temperatureunder reflux for 10 minutes
  2. distillationThen direct distillation

Sources & evidence

ORD record
ord-3a34998ce93b4e13b6fcdf227ccb68a9
Source dataset
uspto-grants-1977_12
Patent number
US04061635

Reaction notes

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