Oxalyl chloride → Ethyl 1-chlorocarbonylcyclopropanecarboxylate

HRID 35269Notes

Reaction equation

HRID 35269 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C:12]1([C:15]([OH:17])=O)[CH2:14][CH2:13]1)=[O:11])[CH3:8]>C1C=CC=CC=1.CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1([C:15]([Cl:4])=[O:17])[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Product 1

HCID 14233946Ethyl 1-chlorocarbonylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

Oxalyl chloride (6.0 g. 47 mmol) was added to a stirred mixture of 1-ethoxycarbonylcyclopropane carboxylic acid (1a) (6 g, 38 mmol) in benzene (25 ml) plus two drops of dimethylformamide. After the gas evolution ceased, the stirring was continued at room temperature for another hour. The reaction mixture was concentrated. The residue was purified by distillation. A fraction collected at 91°-2° C./15 mm was redistilled to give the desired product.

Workup

  1. waitthe stirring was continued at room temperature for another hour
  2. concentrationThe reaction mixture was concentrated
  3. distillationThe residue was purified by distillation
  4. customA fraction collected at 91°-2° C./15 mm
  5. distillationwas redistilled

Sources & evidence

ORD record
ord-ed624e9c145b44959ccc22e3d6dbe760
Source dataset
uspto-grants-1988_08
Patent number
US04766145

Reaction notes

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