Hydroquinone → HCID 21520280, compound

Participants

Reaction Conditions

Reaction Steps

Into a test tube fitted with a cold finger condenser and a nitrogen bypass was put maleic anhydride (1.93 g., 19.7 mmole) and 1,1-dichloro-2-methyl-2-phenylcyclopropane (4.06 g., 20.2 mmole) along with 17.6 mg. hydroquinone. The tube containing the mixture was partially immersed in an oil bath whose temperature was slowly increased. Initial gas evolution was noted at 160°C. (bath). Steady gas evolution occurred at 178°C. with a final heating to 197°C. to insure complete reaction. Total heating time was 6 hours. The product was dissolved in benzene (5 ml.) and the solution was poured into 50 ml. n-hexane. The resultant oil soon crystallized giving 4.65 g (90 percent, m.p. 82°-90°C.) crude product which behaved as a mixture of anhydride and acid. Solution in water gave pure 1-chloro-2-phenylcyclohexene-4,5-dicarboxylic acid (m.p. 187°-189°C.).

Provenance & Evidence