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

HRID 2285663Notes

Reaction equation

HRID 2285663 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].[OH2:17]>N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:13][C:12]([Cl:16])=[CH:7][CH:6]1[O:17][C:3](=[O:10])[CH2:4][C:5]1([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 130201093,3-dimethylpent-4-enoic aicd N,N-dimethylamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst2×

Procedure

31 g (0.2 mole) of 3,3-dimethyl-pent-4 -enoic acid, N,N-dimethylamide are added dropwise, in the course of 3 hours, to a solution of 1 g of azo-bis-isobutyronitrile in 308 g (2 moles) of carbon tetrachloride at 75°-80° C. The mixture is stirred for 1.5 hours at 75°-80° C., a further 1 g of azo-bis-isobutyronitrile is added, and the temperature is maintained for a further 2 hours. After distilling off the unconverted starting materials at a bath temperature not exceeding 150° C., a residue is left, and this is stirred with 100 ml of water at 80°-90° C. for 1 hour. 17 g (0.08 mole) of 5-(2,2-dichlorovinyl)-4,4-dimethyl-tetrahydrofuran-2-one are thereby obtained as a water-insoluble phase.

Workup

  1. temperaturethe temperature is maintained for a further 2 hours
  2. distillationAfter distilling off the
  3. customexceeding 150° C.
  4. waita residue is left
  5. stirringthis is stirred with 100 ml of water at 80°-90° C. for 1 hour

Sources & evidence

ORD record
ord-1475f6d53a004e50a311cbb195e9fe41
Source dataset
uspto-grants-1982_04
Patent number
US04324725

Reaction notes

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