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

HRID 1763957Notes

Reaction equation

HRID 1763957 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C:3]1(C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1N2CCN(CC2)C1>CC1C=CC=CC=1C>[CH3:1][C:2]1([CH3:19])[CH:4]([CH:5]=[C:6]([Cl:7])[Cl:8])[CH:3]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 9237DabcoHCID 14914133Ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 20.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

13 g of diethyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1,1-dicarboxylate were dissolved in 50 g of o-xylene and 20 g of triethylenediamine were added. The mixture was then heated to the boil for 6 hours. After cooling, ice-cold dilute hydrochloric acid was added so that a neutral or weakly acid pH value resulted. The organic phase was separated off and dried with Na2SO4 and the xylene was distilled off in vacuo. The residue weighed 10 g. Fractional distillation gave 2 g of ethyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1-carboxylate as well as 6.7 g of recovered starting material. The yield was thus 40%.

Workup

  1. temperatureThe mixture was then heated to the boil for 6 hours
  2. temperatureAfter cooling
  3. additionice-cold dilute hydrochloric acid was added so that a neutral or weakly acid
  4. customresulted
  5. customThe organic phase was separated off
  6. dry with materialdried with Na2SO4
  7. distillationthe xylene was distilled off in vacuo
  8. distillationFractional distillation

Sources & evidence

ORD record
ord-b3008fc04d884224a3b60cf927c2da4e
Source dataset
uspto-grants-1978_09
Patent number
US04113969

Reaction notes

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