Carbon Tetrachloride → 2(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-

HRID 2285662Notes

Reaction equation

HRID 2285662 reaction equation
CN(C)[C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH:6]=[CH2:7].[C:12]([Cl:16])(Cl)(Cl)[Cl:13].C([O:21]OC(C)(C)C)(C)(C)C>O>[Cl:13][C:12]([Cl:16])=[CH:7][CH:6]1[O:21][C:3](=[O:10])[CH2:4][C:5]1([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 8033Di-tert-butyl peroxideHCID 130201093,3-dimethylpent-4-enoic aicd N,N-dimethylamide

Product 1

HCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-Yield 380%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 40 g (0.26 mole) of 3,3-dimethylpent-4-enoic aicd N,N-dimethylamide, 231 g (1.5 moles) of carbon tetrachloride and 7 g (0.05 mole) of di-tert.-butyl peroxide is stirred for 6 hours at 140° C. in a stainless steel autoclave. 180 g (1.17 mole) of carbon tetrachloride are then distilled from the reaction mixture under reduced pressure, and the residue is stirred with 200 g of water for 1 hour at 80°-90° C. Extraction with methylene chloride, and subsequent distillation of the methylene chloride solution, gives 39 g (0.19 mole) of 5-(2,2-dichlorovinyl)-4,4-dimethyltetrahydrofuran-2-one, of boiling point 101° C./0.27 mbar.

Workup

  1. extractionExtraction
  2. distillationwith methylene chloride, and subsequent distillation of the methylene chloride solution

Sources & evidence

ORD record
ord-13dd550ce60545d794564bec7af82ec6
Source dataset
uspto-grants-1982_04
Patent number
US04324725

Reaction notes

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