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

HRID 1166636Notes

Reaction equation

HRID 1166636 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH2:9]Cl.[I-].[K+].[C:13]([O:19][CH3:20])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>CN(C)C(=O)C>[C:15]([C:14]1([C:13]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8]1)(=[O:16])[CH3:17]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 4875Potassium IodideHCID 7757Methyl acetoacetateHCID 11430Potassium Carbonate

Product 1

HCID 10214400Methyl 1-acetylcyclopropane-1-carboxylateYield 28.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A total of 662.4 g of potassium carbonate, 1161.2 g of 1,2-dichloroethane, 696.7 g of N,N-dimethylacetamide, 33.2 g of potassium iodide, and 464.5 g of methyl acetoacetate were mixed, followed by a reaction at 100° C. for 13 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 washing with the aqueous layer was extracted with 999.7 g of 1,2-dichloroethane. The extract with the organic layer was concentrated under a reduced pressure to distill off 1,2-dichloroethane, was subjected to distillation under a reduced pressure and thereby yielded 160.1 g of methyl 1-acetyl-1-cyclopropanecarboxylate as a colorless liquid as a fraction at 75° C./20 mmHg.

Workup

  1. customfollowed by a reaction at 100° C. for 13 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. extractionThe washing with the aqueous layer was extracted with 999.7 g of 1,2-dichloroethane
  6. extractionThe extract with the organic layer
  7. concentrationwas concentrated under a reduced pressure
  8. distillationto distill off 1,2-dichloroethane
  9. distillationwas subjected to distillation under a reduced pressure

Sources & evidence

ORD record
ord-eb71e80e5d90441993d7b19d682425ac
Source dataset
uspto-grants-2003_09
Patent number
US06613935B2

Reaction notes

Loading…