1,8-Diazabicyclo(5.4.0)undec-7-ene → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

HRID 1763956Notes

Reaction equation

HRID 1763956 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].N12CCCN=C1CCCCC2>C1(C)C(C)=CC=CC=1>[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 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14914133Ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 34.1%

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 xylene (technical grade) and 30 g of 1,8-diaza-bicyclo[5.4.0]undec-7-ene were added. The mixture was then heated to the boil for 8 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 12.2 g. Fractional distillation gave 3.4 g of ethyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1-carboxylate and also 8.0 g of recovered starting material. The yield was thus 87%.

Workup

  1. temperatureThe mixture was then heated to the boil for 8 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-d92f8cceed1f4ec7a8ee2b2d8681379f
Source dataset
uspto-grants-1978_09
Patent number
US04113969

Reaction notes

Loading…