Diethyl (trichloromethyl)phosphonate → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

HRID 2412461Notes

Reaction equation

HRID 2412461 reaction equation
C(OP([C:9]([Cl:12])([Cl:11])Cl)(=O)OCC)C.[CH2:13]([O:15][C:16]([CH:18]1[CH:20]([CH:21]=O)[C:19]1([CH3:24])[CH3:23])=[O:17])[CH3:14].[Mg]>CN(C)C=O>[CH2:13]([O:15][C:16]([CH:18]1[CH:20]([CH:21]=[C:9]([Cl:11])[Cl:12])[C:19]1([CH3:23])[CH3:24])=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 70085Diethyl (trichloromethyl)phosphonateHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25.5 g (0.1 mole) of trichloromethanephosphonic acid diethyl ester and 17.2 g (0.1 mole) of 3-formyl-2,2-dimethyl-cyclopropane-1-carboxylic acid ethyl ester was added dropwise to 9.6 g of activated magnesium filings in 100 ml of dimethylformamide in a manner such that the reaction temperature did not exceed 60° C. When the exothermic reaction had ended, the reaction mixture was allowed to cool to room temperature. It was then filtered. 200 ml of water were added to the filtrate; this solution was extracted twice with 100 ml of methylene chloride each time. The combined methylene chloride extracts were dried over sodium sulphate and filtered. The filtrate was distilled. 3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid ethyl ester was obtained in a yield of 60% of theory.

Workup

  1. customdid not exceed 60° C
  2. customWhen the exothermic reaction
  3. filtrationIt was then filtered
  4. addition200 ml of water were added to the filtrate
  5. extractionthis solution was extracted twice with 100 ml of methylene chloride each time
  6. dry with materialThe combined methylene chloride extracts were dried over sodium sulphate
  7. filtrationfiltered
  8. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-c0039e41640d4216b9cc860ae1672ec7
Source dataset
uspto-grants-1985_01
Patent number
US04492800

Reaction notes

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