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

HRID 2295253Notes

Reaction equation

HRID 2295253 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([CH:9]=O)[C:7]1([CH3:12])[CH3:11])=[O:5])[CH3:2].P(OCC)(OCC)OCC.[Cl:23][C:24](Cl)([Cl:28])C([O-])=O.[Na+].O>COCCOCCOC>[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:24]([Cl:28])[Cl:23])[C:7]1([CH3:12])[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 31215Triethyl phosphiteHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 23681045Sodium Trichloroacetate

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 17.0 g (0.1 mole) of 3-formyl-2,2-dimethyl-cyclopropane-1-carboxylic acid ethyl ester, 16.6 g (0.1 mole) of triethyl phosphite and 18.5 g (0.1 mole) of sodium trichloroacetate in 100 ml of diglyme was heated to 150° C. under argon for 6 hours. The reaction mixture was then poured into water. Extraction with 2 portions of 100 ml each of methylene chloride followed. The combined methylene chloride extracts were dried over sodium sulphate. 3-(2,2-Dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid ethyl ester was obtained as a crude product in a yield of 73% of theory.

Workup

  1. extractionExtraction with 2 portions of 100 ml each of methylene chloride
  2. dry with materialThe combined methylene chloride extracts were dried over sodium sulphate

Sources & evidence

ORD record
ord-f2c48f19508e4c3e8e097116342aebd8
Source dataset
uspto-grants-1984_01
Patent number
US04424166

Reaction notes

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