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

HRID 991264Notes

Reaction equation

HRID 991264 reaction equation
Cl[CH2:2][CH2:3]Cl.C(=O)([O-])[O-].[K+].[K+].[C:11]([O:18][CH3:19])(=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:12]1([C:11]([O:18][CH3:19])=[O:17])([C:13]([O:15][CH3:16])=[O:14])[CH2:3][CH2:2]1

Participants

6

Reactant 3

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

Product 1

HCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

319.6 g of 1,2-dichloroethane (3.23 mol), 5 g of polyethylene glycol (mean molar mass 600 g/mol) and 168.0 g of potassium carbonate (1.2 mol) were initially introduced, and the reaction mixture was heated until the 1,2-dichloroethane refluxes. 132.1 g of dimethyl malonate (1 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 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 87%.

Workup

  1. customfor 6 hours
  2. customwas removed by azeotropic distillation with 1,2-dichloroethane throughout the reaction

Sources & evidence

ORD record
ord-eee69666542248a59bf699dc65a2a420
Source dataset
uspto-grants-2002_10
Patent number
US06462224B2

Reaction notes

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