Water → 3-Chlorobenzocyclobutene-1-carboxylic acid

HRID 2372757Notes

Reaction equation

HRID 2372757 reaction equation
[Cl:1][C:2]1[C:9]2[CH2:8][CH:7]([C:10]#N)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:12].[K+].[OH2:14]>C(O)C>[Cl:1][C:2]1[C:9]2[CH:8]=[C:7]([C:10]([OH:14])=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 135607112-Chlorobicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

Product 1

HCID 198863753-Chlorobenzocyclobutene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 3-chloro-1-cyanobenzocyclobutane (prepared according to the process described in Patent EP 119,107) are added to a solution of 6.0 g of potassium hydroxide in 58 ml of ethanol. The mixture is stirred at room temperature overnight. 7.5 ml of water are then added and the mixture is heated to reflux for 6 hours. The ethanol is evaporated off to dryness. The residue is taken up with water and the aqueous phase is washed with ethyl ether, then acidified (pH 1) with 1N hydrochloric acid and extracted with dichloromethane. The organic phase is dried, filtered and evaporated to dryness.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 6 hours
  3. customThe ethanol is evaporated off to dryness
  4. washthe aqueous phase is washed with ethyl ether
  5. extractionextracted with dichloromethane
  6. customThe organic phase is dried
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-ac3c7d82db414898ab0a0bf7efd04f48
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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