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

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Reaction Steps

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).

Provenance & Evidence