Hydrochloric Acid → 5-Hexenoic acid, 4,6,6-trichloro-3,3-dimethyl-, methyl ester

HRID 358534Notes

Reaction equation

HRID 358534 reaction equation
[ClH:1].[CH3:2][C:3]1([CH3:13])[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[O:7][C:5](=[O:6])[CH2:4]1.[CH3:14]O>>[CH3:2][C:3]([CH3:13])([CH:8]([Cl:1])[CH:9]=[C:10]([Cl:12])[Cl:11])[CH2:4][C:5]([O:7][CH3:14])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 101982032(3H)-Furanone, 5-(2,2-dichloroethenyl)dihydro-4,4-dimethyl-

Product 1

HCID 109997915-Hexenoic acid, 4,6,6-trichloro-3,3-dimethyl-, methyl esterYield 96%

Procedure

To 30 parts of methanol saturated with hydrogen chloride gas (concentration of hydrogen chloride: about 50%) was added 41.8 parts of 3,3-dimethyl-4-(2',2'-dichlorovinyl)-4-butanolide, followed by heating in a closed tubular reactor at 70°-80° C. for 3 hours. The reaction mixture was then treated in the same manner as Example 1. By the above procedure was obtained 49.8 parts of methyl 3,3-dimethyl-4,6,6-trichloro-5-hexenoate (yield 96%). This product was found to have properties identical with those of the product according to Example 1.

Workup

  1. temperatureby heating in a closed tubular reactor at 70°-80° C. for 3 hours
  2. additionThe reaction mixture was then treated in the same manner as Example 1

Sources & evidence

ORD record
ord-6d72b0426bbf4a80a333109f6f672509
Source dataset
uspto-grants-1984_08
Patent number
US04468521

Reaction notes

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