Ethyl diazoacetate → Ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 2049818Notes

Reaction equation

HRID 2049818 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>CCOCC.[Cu]>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2([CH3:9])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 20344578HCID 20344578, compound

Product 1

HCID 20344552Ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-(4-chlorophenoxy)-2-methyl-2-propene (4.5 g, 0.032 mol) and 0.158 g of copper powder is heated at 110° for 30 min; then 2.78 g ethyl diazoacetate (0.025 mol) is added dropwise, keeping the temperature at 110°. After the addition is complete (approximately 30 min), the mixture is stirred at 110° until nitrogen evolution is complete. The mixture is cooled, diluted with ether, filtered and concentrated. Distillation of the residue yields ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. temperatureis heated at 110° for 30 min
  2. customat 110°
  3. additionAfter the addition
  4. custom(approximately 30 min)
  5. temperatureThe mixture is cooled
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-029931d34aca4c5883606f563501ed51
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

Loading…