Isobutylene → 2-Chloro-3,3-dimethyl-2-(2,2,2-trichloroethyl)cyclobutan-1-one

HRID 127176Notes

Reaction equation

HRID 127176 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[Cl:5][CH:6]([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[C:7](Cl)=[O:8].C(N(CC)CC)C>C1CCCCC1>[Cl:5][C:6]1([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[C:2]([CH3:4])([CH3:3])[CH2:1][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 8471TriethylamineHCID 30178312,4,4,4-Tetrachlorobutanoyl chloride

Product 1

HCID 125465452-Chloro-3,3-dimethyl-2-(2,2,2-trichloroethyl)cyclobutan-1-oneYield 60.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

In an autoclave, 280 g of isobutylene are added under pressure to 122 g (0.5 mole) of 2,4,4,4-tetrachlorobutyryl chloride in 600 ml of cyclohexane. A solution of 51 g (0.5 mole) of triethylamine in 500 ml of cyclohexane is then pumped in at 65° C. The reaction mixture is then kept for 3 hours at 65° C. The precipitated hydrochloride of triethylamine is collected by filtration and the filtrate is concentrated. The resulting crystals are collected by filtration, affording 79.4 g of 2-chloro-2-(2',2',2'-trichloroethyl)-3,3-dimethylcyclobutan-1-one with a melting point of 75°-76° C. (60% of theory).

Workup

  1. customis then pumped in at 65° C
  2. filtrationThe precipitated hydrochloride of triethylamine is collected by filtration
  3. concentrationthe filtrate is concentrated
  4. filtrationThe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-882b634bda92417ba32e4498f90b8a76
Source dataset
uspto-grants-1981_03
Patent number
US04255351

Reaction notes

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