5-Hexenoic acid, 4,6,6-trichloro-3,3-dimethyl-, methyl ester → 2(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-

HRID 358535Notes

Reaction equation

HRID 358535 reaction equation
[CH3:1][C:2]([CH3:14])([CH:8](Cl)[CH:9]=[C:10]([Cl:12])[Cl:11])[CH2:3][C:4]([O:6]C)=[O:5].CC(C)(C=CC(Cl)(Cl)Cl)CC(OC)=O>>[CH3:1][C:2]1([CH3:14])[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[O:6][C:4](=[O:5])[CH2:3]1

Participants

3

Reactant 2

HCID 109997915-Hexenoic acid, 4,6,6-trichloro-3,3-dimethyl-, methyl ester2×HCID 53438825Methyl 6,6,6-trichloro-3,3-dimethylhex-4-enoate

Product 1

HCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-Yield 11%

Procedure

The procedure of Example 11 was repeated except that a mixture of 26.0 parts of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate and 26.0 parts of methyl 3,3-dimethyl-6,6,6-trichloro-4-hexenoate (mole ratio=1:1) was used in lieu of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate to obtain 37.9 parts of methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl) cyclopropanecarboxylate (yield 85% based on starting material; cis/trans ratio=29:71) and 4.6 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide (yield 11% based on starting material). The latter compound 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide (4.6 parts) was treated with 5.0 parts of a methanolic solution of hydrogen chloride (concentration of hydrogen chloride: about 50%) to obtain 5.5 parts of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate (yield 96% based on 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide).

Sources & evidence

ORD record
ord-77098f4474a5478a8cdfa2702543c107
Source dataset
uspto-grants-1984_08
Patent number
US04468521

Reaction notes

Loading…