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

HRID 224754

反応式

HRID 224754 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4b67b80acfad4f38a42f2895b3a26a95
出典データセット
uspto-grants-1980_11
特許番号
US04234517

関連ノート

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