Water → 1-(2,2-Dichlorovinyl)-2-acetyl-3,3-dimethylcyclopropane

HRID 66545Notes

Reaction equation

HRID 66545 reaction equation
C(OP([CH:9]([Cl:11])[Cl:10])(=O)OCC)C.[C:12]([CH:15]1[C:17]([CH3:19])([CH3:18])[CH:16]1[CH:20]=O)(=[O:14])[CH3:13].O>CN(C)C=O.O1CCCC1>[Cl:11][C:9]([Cl:10])=[CH:20][CH:16]1[C:17]([CH3:19])([CH3:18])[CH:15]1[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 11085347Phosphonic acid, (dichloromethyl)-, diethyl esterHCID 14309614HCID 14309614, compound

Product 1

HCID 145714121-(2,2-Dichlorovinyl)-2-acetyl-3,3-dimethylcyclopropaneYield 71.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12.3 g (0.11 mol) of potassium tert.-butylate in 30 ml of dimethylformamide was added dropwise, under an inert gas atmosphere (nitrogen or argon) at -20° to -25° C., to a solution of 24 g (0.180 mol) of dichloromethane-phosphonic acid diethyl ester and 14 g (0.1 mol) of 2-acetyl-3,3-dimethylcyclopropanecarboxaldehyde in 100 ml of tetrahydrofuran. The mixture was subsequently stirred for 3 hours without cooling, 200 ml of water were added and extraction was carried out twice with 100 ml of methylene chloride. The organic phase was washed with 50 ml of 10% strength sodium hydroxide solution and then with 3 times 50 ml of water, dried over sodium sulphate and evaporated in vacuo. 14.8 g (71% of theory) of 1-(2,2-dichlorovinyl)-2-acetyl-3,3-dimethylcyclopropane were obtained from the residue, by vacuum distillation, in the form of a pale yellow oil having a boiling point of 55°-57° C./0.3 mbar.

Workup

  1. temperaturewithout cooling
  2. extractionextraction
  3. washThe organic phase was washed with 50 ml of 10% strength sodium hydroxide solution
  4. dry with materialwith 3 times 50 ml of water, dried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8c38356c947d476ea52a137cea69d943
Source dataset
uspto-grants-1982_08
Patent number
US04342704

Reaction notes

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