Ethanol → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

HRID 224754

Reaction equation

HRID 224754 reaction equation
[CH3:1][C:2]([CH3:14])([CH:8](O)[CH:9]=[C:10]([Cl:12])[Cl:11])[CH2:3][CH2:4]C(O)=O.S(Cl)(Cl)=[O:16].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:4]([CH:3]1[C:2]([CH3:1])([CH3:14])[CH:8]1[CH:9]=[C:10]([Cl:11])[Cl:12])=[O:16])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 233302513,3-Dimethyl-4-hydroxy-6,6-dichlorohex-5-enecarboxylic acid

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 81%

Procedure

5.25 g (0.025 mol) of the lactone of 3,3-dimethyl-4-hydroxy-6,6-dichlorohex-5-enecarboxylic acid with 15 ml of thionyl chloride is held for 3 hours at 70° C. An addition of 20 ml of ethanol is then made, and the reaction mixture is allowed to stand for 14 hours at room temperature. The reaction mixture is concentrated by evaporation, and the residue is treated briefly with sodium ethylate in ethanol, as described in Example 3. After customary processing, there is obtained in 81% yield the 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylic acid ethyl ester having a cis-trans ratio of approximately 1:4, determined according to NMR spectrum.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionthe residue is treated briefly with sodium ethylate in ethanol

Sources & evidence

ORD record
ord-4b67b80acfad4f38a42f2895b3a26a95
Source dataset
uspto-grants-1980_11
Patent number
US04234517

Linked notes

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