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

HRID 1680800

Reaction equation

HRID 1680800 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(C(OCC)=O)[CH:8]([CH:9]=[C:10]([Cl:12])[Cl:11])[C:7]1([CH3:14])[CH3:13])=[O:5])[CH3:2].O=P1(C)CCC=C1.[Cl-].[Na+]>O>[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:10]([Cl:11])[Cl:12])[C:7]1([CH3:13])[CH3:14])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 701042,3-Dihydro-1-methyl-1H-phosphole 1-oxideHCID 14914133Ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

30 g (0.1 mol) of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1,1-dicarboxylic acid diethyl ester, 50 ml of 1-oxo-1-methyl-phospholine, 6 g of sodium chloride and 4 ml of water were heated to 175° C. for 9 hours. The mixture was then cooled, poured into 150 ml of water and extracted with petroleum ether. After drying with MgSO4, the mixture was fractionally distilled. 21.3 g (=90% of theory) of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1-carboxylic acid ethyl ester of boiling point 65°-75° C./0.1 mm Hg were obtained. 49.7 g of 1-oxo-1-methyl-phospholine of boiling point 75°-77° C./0.15 mm Hg were recovered by fractional distillation of the aqueous phase.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with petroleum ether
  3. dry with materialAfter drying with MgSO4
  4. distillationthe mixture was fractionally distilled

Sources & evidence

ORD record
ord-fc7aa8eebf7d4aa594b72af9cf0a8909
Source dataset
uspto-grants-1981_06
Patent number
US04276225

Linked notes

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