Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl ester → 2(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-

HRID 358539Notes

Reaction equation

HRID 358539 reaction equation
[CH3:1][C:2]([CH3:16])([CH:9](Br)[CH2:10][C:11](Cl)([Cl:13])[Cl:12])[CH2:3][C:4]([O:6]CC)=[O:5].CC(C)(C(Cl)CC(Cl)(Cl)Cl)CC(OCC)=O>>[CH3:1][C:2]1([CH3:16])[CH:9]([CH:10]=[C:11]([Cl:13])[Cl:12])[O:6][C:4](=[O:5])[CH2:3]1

Participants

3

Reactant 2

HCID 108412Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl esterHCID 12607835Ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate

Product 1

HCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-Yield 90%

Procedure

The procedure of Reference Example 1 was repeated except that 35.4 parts of ethyl 3,3-dimethyl-4-bromo-6,6,6-trichlorohexanoate was used in lieu of ethyl 3,3-dimethyl-4,6,6,6-tetrachlorohexanoate. By this procedure was obtained 19.0 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide (yield 90%).

Sources & evidence

ORD record
ord-397b0a7c55284e67ba8f917355e50890
Source dataset
uspto-grants-1984_08
Patent number
US04468521

Reaction notes

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