1,2-Dichloroethane → 1,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

HRID 991263Notes

Reaction equation

HRID 991263 reaction equation
Cl[CH2:2][CH2:3]Cl.COCCO.C(=O)([O-])[O-].[K+].[K+].[C:16]([O:23][CH3:24])(=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:17]1([C:16]([O:23][CH3:24])=[O:22])([C:18]([O:20][CH3:21])=[O:19])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 7943Dimethyl malonateHCID 80192-MethoxyethanolHCID 11430Potassium Carbonate

Product 1

HCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

296.9 g of 1,2-dichloroethane (3 mol), 5 g of polyethylene glycol monomethyl ether (mean molar mass 550 g/mol) and 177.1 g of potassium carbonate (1.265 mol) were initially introduced, and the reaction mixture was heated until the 1,2-dichloroethane refluxes. 125.5 g of dimethyl malonate (0.95 mol) and 1.25 g of tetrabutylammonium bromide (3.88 mmol) were then added at the boil. The mixture was stirred using a paddle stirrer for 6.5 hours. Water formed during the reaction was removed by azeotropic distillation with 1,2-dichloroethane throughout the reaction. Further work-up was carried out analogously to Comparative Example 2. The yield was 95%.

Workup

  1. customfor 6.5 hours
  2. customwas removed by azeotropic distillation with 1,2-dichloroethane throughout the reaction

Sources & evidence

ORD record
ord-d3ea3b7cfef140e9bb92f46ccd97f3d4
Source dataset
uspto-grants-2002_10
Patent number
US06462224B2

Reaction notes

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