1,2-Dichloroethane → Ethyl 1-acetylcyclopropane-1-carboxylate

HRID 1166635Notes

Reaction equation

HRID 1166635 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH2:9]Cl.[I-].[K+].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>CN(C)C(=O)C>[C:15]([C:14]1([C:13]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9][CH2:8]1)(=[O:16])[CH3:17]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 4875Potassium IodideHCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 33.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A total of 165.6 g of potassium carbonate, 390.0 g of 1,2-dichloroethane, 234.0 g of N,N-dimethylacetamide, 5.0 g of potassium iodide, and 78.0 g of ethyl acetoacetate were mixed, followed by a reaction at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and was filtrated, the resulting filtrate was washed with two portions of 5% by weight hydrochloric acid, and the organic layer was washed with water. The organic layer was then concentrated under a reduced pressure to distill off 1,2-dichloroethane, was subjected to distillation under a reduced pressure and thereby yielded 31.7 g of ethyl 1-acetyl-1-cyclopropanecarboxylate as a colorless liquid as a fraction at 80° C./20 mmHg.

Workup

  1. customfollowed by a reaction at 100° C. for 4 hours
  2. filtrationwas filtrated
  3. washthe resulting filtrate was washed with two portions of 5% by weight hydrochloric acid
  4. washthe organic layer was washed with water
  5. concentrationThe organic layer was then concentrated under a reduced pressure
  6. distillationto distill off 1,2-dichloroethane
  7. distillationwas subjected to distillation under a reduced pressure

Sources & evidence

ORD record
ord-e881e2aefc1844d19c6935a49283d94e
Source dataset
uspto-grants-2003_09
Patent number
US06613935B2

Reaction notes

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