Acetic Acid → 1,1,5-Trichloro-3,3-dimethylpent-1-ene

HRID 1462649Notes

Reaction equation

HRID 1462649 reaction equation
[Cl-:1].[Al+3].[Cl-:3].[Cl-].[Cl:5][CH2:6][CH2:7][C:8](Cl)([CH3:10])[CH3:9].[C:12](O)(=O)[CH3:13]>ClC(Cl)=C>[CH3:9][C:8]([CH3:10])([CH2:13][CH2:12][Cl:3])[CH:7]=[C:6]([Cl:1])[Cl:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 693581,3-Dichloro-3-methylbutaneHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 155843271,1,5-Trichloro-3,3-dimethylpent-1-ene

Reagents, catalysts & solvents 1

HCID 6366Vinylidene chlorideSolvent

Conditions

Temperature
-10 °C

Procedure

20 g of aluminum chloride are dissolved in 2,300 g of 1,1-dichloroethene, while stirring and cooling to -10° C. Thereupon, 1,286 g of 1,3-dichloro-3-methylbutane are added dropwise in the course of 3 hours, and simultaneously, at intervals of 15 minutes, further 3 g portions of aluminum chloride are added in measured amounts to the mixture, a reaction temperature of between 0° and +5° C. being maintained by cooling. After the end of the reaction, 60 ml of acetic acid are added dropwise to the reaction mixture. Thereafter, the product mixture is filtered over sodium sulphate, and is then metered into a distillation apparatus, the trough temperature being kept at 120° C., and a pressure of 1 mbar being maintained; the distillate is cooled and condensed by means of a dry ice/acetone mixture. The crude distillate is then fractionally distilled in vacuo in a Vigreux column. 1,650 g of 3,3-dimethyl-1,1,5-trichloro-1-pentene of boiling point 59° to 63° C./0.1 mm Hg are obtained. 1,1-Dichloro-3,3-dimethyl-1,4-pentadiene

Workup

  1. temperaturea reaction temperature of between 0° and +5° C. being maintained
  2. temperatureby cooling
  3. additionare added dropwise to the reaction mixture
  4. filtrationThereafter, the product mixture is filtered over sodium sulphate
  5. custombeing kept at 120° C.
  6. temperaturea pressure of 1 mbar being maintained
  7. temperaturethe distillate is cooled
  8. customcondensed by means of a dry ice/acetone mixture
  9. distillationThe crude distillate is then fractionally distilled in vacuo in a Vigreux column

Sources & evidence

ORD record
ord-144bfc7d8e8445cfb7999a9774832d8c
Source dataset
uspto-grants-1984_07
Patent number
US04460793

Reaction notes

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