Ethanol → Cyclohex-2-ene-1,2-dicarboxylic acid

Participants

Reaction Steps

A stirred solution of 12.0 grams (0.067 mole) of ethyl 2-cyanocyclohex-2-enecarboxylate (prepared by the method of G. Kon and B. Nandi, JCS, 1628-1633 (1933), and 75 ml of aqueous 30% potassium hydroxide in approximately 20 ml of ethanol was heated under reflux for 16 hours. The reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was cooled in an ice bath, and the pH was adjusted to 2 with sulfuric acid. The resultant precipitate was collected by filtration and was dried to yield 5.0 grams of cyclohexene-2,3-dicarboxylic acid; m.p. 201°-203° C.

Provenance & Evidence