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

HRID 1703060Notes

Reaction equation

HRID 1703060 reaction equation
CN(P(N(C)C)N(C)C)C.C(OP([C:19]([Cl:22])([Cl:21])Cl)(=O)OCC)C.[CH2:23]([O:25][C:26]([CH:28]1[CH:30]([CH:31]=O)[C:29]1([CH3:34])[CH3:33])=[O:27])[CH3:24]>O>[CH2:23]([O:25][C:26]([CH:28]1[CH:30]([CH:31]=[C:19]([Cl:21])[Cl:22])[C:29]1([CH3:33])[CH3:34])=[O:27])[CH3:24]

Participants

5

Reactant 3

HCID 15355Hexamethylphosphorous triamideHCID 70085Diethyl (trichloromethyl)phosphonateHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

16.3 g (0.1 mole) of tris-dimethylaminophosphine were added dropwise to 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 at a temperature of 40° C. The reaction mixture was then warmed to 90° C. for 3 to 4 hours. It was subsequently cooled and poured into 200 ml of water. This suspension was extracted twice with 100 ml of methylene chloride each time. The combined extracts were dried over sodium sulphate and then concentrated. 3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid ethyl ester was obtained in a yield of 88% of theory.

Workup

  1. temperatureIt was subsequently cooled
  2. extractionThis suspension was extracted twice with 100 ml of methylene chloride each time
  3. dry with materialThe combined extracts were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32139ff897d649c78470b13b9f78d01f
Source dataset
uspto-grants-1982_09
Patent number
US04350824

Reaction notes

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