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

HRID 1462096Notes

Reaction equation

HRID 1462096 reaction equation
[OH-].[Na+].O.CO.[CH3:6][C:7]([CH3:21])([CH:14](Cl)[CH2:15][C:16](Cl)([Cl:18])[Cl:17])[CH2:8][C:9]([O:11]CC)=[O:10]>CCOCC>[CH3:6][C:7]1([CH3:21])[CH:14]([CH:15]=[C:16]([Cl:18])[Cl:17])[O:11][C:9](=[O:10])[CH2:8]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 108412Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl ester

Product 1

HCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-Yield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixed solution of 12.0 parts of sodium hydroxide, 40 parts of water and 60 parts of methanol was added dropwise under reflux 31.0 parts of ethyl 3,3-dimethyl-4,6,6,6-tetrachlorohexanoate and, after the dropwise addition had been completed, the mixture was stirred at that temperature for 2 hours. The reaction mixture was then distilled under reduced pressure to remove the methanol, and the residue was neutralized with hydrochloric acid and extracted with diethyl ether. From this ether layer was obtained 19.2 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide (yield 92%) which had the following properties.

Workup

  1. additionafter the dropwise addition
  2. distillationThe reaction mixture was then distilled under reduced pressure
  3. customto remove the methanol
  4. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-c508fe23703e4e678e9ad321d4ed3d36
Source dataset
uspto-grants-1984_07
Patent number
US04458090

Reaction notes

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