Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate → 2(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-

HRID 358540Notes

Reaction equation

HRID 358540 reaction equation
[CH3:1][C:2]([CH3:15])([CH:9](Cl)[CH:10]=[C:11]([Cl:13])[Cl:12])[CH2:3][C:4]([O:6]CC)=[O:5].CC(C)(C(Cl)C=C(Cl)Cl)CC(OC)=O>>[CH3:1][C:2]1([CH3:15])[CH:9]([CH:10]=[C:11]([Cl:13])[Cl:12])[O:6][C:4](=[O:5])[CH2:3]1

Participants

3

Reactant 2

HCID 3042523Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoateHCID 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 95%

Procedure

The above procedure was repeated except that 27.4 parts of ethyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate was used in lieu of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate. In this case, 19.8 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide was obtained (yield 95%).

Sources & evidence

ORD record
ord-af22ec5b42ba4adeb1f9266970015679
Source dataset
uspto-grants-1984_08
Patent number
US04468521

Reaction notes

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