Hydrochloric Acid → 1-(2,2-Dichlorovinyl)-1-ethylcyclopentane

HRID 2412447Notes

Reaction equation

HRID 2412447 reaction equation
[Cl:1][C:2]([Cl:4])=[CH2:3].[CH2:5]([C:7]1(Cl)[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:6].Cl>[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>[Cl:1][C:2]([Cl:4])=[CH:3][C:7]1([CH2:5][CH3:6])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6366Vinylidene chlorideHCID 128595681-Chloro-1-ethylcyclopentane

Product 1

HCID 132091911-(2,2-Dichlorovinyl)-1-ethylcyclopentaneYield 82%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

10 g of anhydrous aluminum chloride were added to 291 g (3 mols) of 1,1-dichloroethene at -20° C., and thereafter 133 g (1 mol) of 1-ethyl-cyclopentyl chloride (Chem. Abstr. 42, 6238 (1948)) were added dropwise at 0° to 10° C. The reaction solution was allowed to warm up to 20° C., a further 5 g of aluminum chloride was added, and the mixture was stirred for a further 2 hours at 20° C. The mixture was poured on to ice, and was worked up with methylene chloride and dilute hydrochloric acid. 158 g (82% of theory) of 1-(2,2-dichlorovinyl)-1-ethyl-cyclopentane of boiling point 45° to 50° C./0.1 mm Hg were obtained by fractional distillation of the organic phase after the latter had been dried over sodium sulphate.

Workup

  1. additionThe mixture was poured on to ice

Sources & evidence

ORD record
ord-cc1e0d3af5ba4c158497c5ac338c38b5
Source dataset
uspto-grants-1985_01
Patent number
US04492795

Reaction notes

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