Water → Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid

HRID 370571

Reaction equation

HRID 370571 reaction equation
[Cl:1][C:2](Cl)([Cl:12])[CH:3]1[CH:8]2[CH:6]([C:7]2([CH3:10])[CH3:9])[C:5](=[O:11])[O:4]1.O>C(O)(=O)C.CCOCC.[Zn]>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:8]1[C@H:6]([C:5]([OH:11])=[O:4])[C:7]1([CH3:9])[CH3:10]

Participants

6

Reactant 2

HCID 962WaterHCID 125252184-Trichloromethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane

Product 1

HCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acidYield 97%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of zinc powder (0.52 g, 0.008 mole) in 0.6 ml of acetic acid and 3 ml of ether was added dropwise over a period of 15 minutes a solution of 4-trichloromethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane (0.487 g, 0.002 mole) in 3 ml of ether. The mixture was stirred for two hours at room temperature, 30 ml of ether and 5 ml of water were added, and the mixture was then filtered through Celite filter aid. The organic layer was separated, washed twice with saturated aqueous sodium chloride, dried over magnesium sulfate, and the ether was evaporated to give crystalline cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (0.405 g, 97% yield).

Workup

  1. filtrationthe mixture was then filtered through Celite
  2. filtrationfilter aid
  3. customThe organic layer was separated
  4. washwashed twice with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customthe ether was evaporated

Sources & evidence

ORD record
ord-b63ab4da8f0b40aa9d73b6f54d968290
Source dataset
uspto-grants-1985_07
Patent number
US04526987

Linked notes

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