Dichloromethane → 1-Chloro-4-acetyl-cyclohexene

HRID 414649

Reaction equation

HRID 414649 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl.[CH2:13]=[CH:14][C:15]([Cl:17])=[CH2:16]>O>[Cl:17][C:15]1[CH2:14][CH2:13][CH:1]([C:3](=[O:4])[CH3:5])[CH2:2][CH:16]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6570Methyl vinyl ketoneHCID 31369ChloropreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 143656601-Chloro-4-acetyl-cyclohexene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 98.1 parts of methyl vinyl ketone, 187 parts of anhydrous aluminum chloride and 1980 parts of methylene chloride was added 123 parts of chloroprene and the mixture was stirred at 25° C. for three hours and left standing for another 16 hours. Water was added to the reaction mixture and the organic layer was washed with 5% hydrochloric acid. Distillation gave a center cut of 61 parts of 1-chloro-4-acetyl-cyclohexene (125°-6° C./20 mm Hg). Reference: A. A. Petrov and N. P. Sopov, CA 42, 1910h (1948).

Workup

  1. waitleft
  2. waitstanding for another 16 hours
  3. washthe organic layer was washed with 5% hydrochloric acid
  4. distillationDistillation

Sources & evidence

ORD record
ord-19e3802694574392bda66521ea4de726
Source dataset
uspto-grants-1988_12
Patent number
US04792618

Linked notes

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