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

HRID 1462098Notes

Reaction equation

HRID 1462098 reaction equation
[OH-].[Na+].O.[CH3:4][C:5]([CH3:17])([CH:11](Cl)[CH:12]=[C:13]([Cl:15])[Cl:14])[CH2:6][C:7]([O:9]C)=[O:8]>CO>[CH3:4][C:5]1([CH3:17])[CH:11]([CH:12]=[C:13]([Cl:15])[Cl:14])[O:9][C:7](=[O:8])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 109997915-Hexenoic acid, 4,6,6-trichloro-3,3-dimethyl-, methyl ester

Product 1

HCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-Yield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed solution of 6.0 parts of sodium hydroxide, 40 parts of water and 60 parts of methanol was added dropwise under reflux 26.0 parts of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate and, after the dropwise addition had been completed, the mixture was further stirred under reflux for 2 hours. The reaction mixture was then treated in the same manner as Reference Example 1 to obtain 19.5 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide (yield 93%).

Workup

  1. additionafter the dropwise addition
  2. temperatureunder reflux for 2 hours
  3. additionThe reaction mixture was then treated in the same manner as Reference Example 1

Sources & evidence

ORD record
ord-7eb85fbbc3304d4d93b54f9ba652a51b
Source dataset
uspto-grants-1984_07
Patent number
US04458090

Reaction notes

Loading…