Methane → HCID 21387599, compound

Participants

Reaction Conditions

Reaction Steps

5-(2-Methylbenzoyl)-2-furoic acid [prepared as described in (e) above; 96.6 g.] was added to a solution of potassium hydroxide (70 g.) in diethylene glycol (530 ml.) at 100°-110° C. When the solution was complete, hydrazine hydrate (58%; 53 ml.) was added. The mixture was gradually warmed and then maintained under reflux at 145° C. for 7 hours. Evolution of nitrogen was monitored by collecting the gas over water. Evolution of nitrogen did not completely cease. The reaction mixture was cooled, diluted with water (600 ml.) and stirred while acidifying by dropwise addition of concentrated hydrochloric acid to give crude 5-(2- methylbenzyl)-2-furoic acid in the form of a sticky, brown coloured solid, which was collected, washed with water and dried. The solid thus obtained was dissolved in a mixture of saturated aqueous sodium bicarbonate solution (420 ml.) and water (420 ml.), treated with charcoal and filtered. The filtrate was acidified by the dropwise addition, with stirring, of concentrated hydrochloric acid until the powdery precipitate began to become sticky. The addition of a little 2N aqueous sodium carbonate solution removed this stickiness and a white powdery solid was collected, washed with water and dried to give 5-(2-methylbenzyl)-furoic acid (39 g.), m.p. 136°-138° C., raised to 139°-141° C. by recrystallisation from light petroleum (b.p. 100°-120° C.).

Provenance & Evidence