Sodium Hydroxide → 3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid

HRID 2059157Notes

Reaction equation

HRID 2059157 reaction equation
Br[C:2]([Br:13])([Br:12])[CH2:3][CH:4]1[C:7]([CH3:9])([CH3:8])[CH:6](Cl)[C:5]1=[O:11].[OH-:14].[Na+]>>[Br:13][C:2]([Br:12])=[CH:3][CH:4]1[C:7]([CH3:8])([CH3:9])[CH:6]1[C:5]([OH:11])=[O:14]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 125872302-Chloro-3,3-dimethyl-4-(2,2,2-tribromoethyl)cyclobutan-1-one

Product 1

HCID 1812483-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acidYield 100%

Conditions

Temperature
80 °C

Procedure

A mixture of 800 mg (0.02 mole) of 2-(2',2',2'-tribromoethyl)-3,3-dimethyl-4-chlorocyclobutan-1-one and 5.6 ml of 5% by weight of aqueous sodium hydroxide solution is stirred for 18 hours at 0° C. and subsequently for one additional hour at 80° C. Then the reaction mixture is cooled to room temperature washed with diethyl ether, acidified with concentrated hydrochloric acid and extracted with diethyl ether. The extract is washed with water and dried over magnesium sulphate. After evaporation of the diethyl ether there is obtained 0.59 g (100% of theoriy) of 2-(2',2'-dibromovinyl)-3,3-dimethylcyclopropane-1-carboxylic acid consisting to 80% of the cis-isomer and to 20% of the trans-isomer.

Workup

  1. temperatureThen the reaction mixture is cooled to room temperature
  2. washwashed with diethyl ether
  3. extractionextracted with diethyl ether
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporation of the diethyl ether

Sources & evidence

ORD record
ord-3bab2ea77fd34a62b37e6b6c75198634
Source dataset
uspto-grants-1982_03
Patent number
US04322374

Reaction notes

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