Water → 2-Chlorobicyclo(4.2.0)octa-1(6),2,4-triene-7-carboxylic acid

HRID 1026625Notes

Reaction equation

HRID 1026625 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH:9]([C:10]#N)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:12].[K+].[OH2:14]>CCO>[Cl:1][C:2]1[C:7]2[CH2:8][CH:9]([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 102617682-Chlorobicyclo(4.2.0)octa-1(6),2,4-triene-7-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-chloro-1,2-dihydrocyclobutabenzene-1-carbonitrile (196 mmol, 32 g) and potassium hydroxide (978 mmol, 54.9 g) in EtOH (500 ml)/water (100 ml) was stirred at reflux for 2 h. After evaporation of the organic solvent, the aqueous residue was washed with Et2O. The organic layer was extracted with 2N NaOH aq. and combined aqueous layers were acidified with 5 N HCl and extracted with Et2O. The extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was washed with heptane/Et2O (5/1) to afford 3-chloro-1,2-dihydrocyclobutabenzene-1-carboxylic acid (85% yield, 30.3 g).

Workup

  1. temperatureat reflux for 2 h
  2. customAfter evaporation of the organic solvent
  3. washthe aqueous residue was washed with Et2O
  4. extractionThe organic layer was extracted with 2N NaOH aq. and combined aqueous layers
  5. extractionextracted with Et2O
  6. washThe extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with heptane/Et2O (5/1)

Sources & evidence

ORD record
ord-e6447b9dbd21416fb32fc10f838abec5
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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