Formaldehyde → HCID 13121256, compound

Participants

Reaction Steps

Phenylhydrazine (108.14 g, 1 mole) is added dropwise to a cooled (4°-8° C.) and stirred mixture of concentrated sulfuric acid (147 g, 1.5 moles), glacial acetic acid (200 ml) and water (25 ml). Paraformaldehyde (30.03 g, 1 mole) and phenylethylene (104.1 g, 1 mole) are added simultaneously during 1 hr at 25° C. and stirring is continued for 2 hr at 30° C. Water (500 ml) is added and the aqueous dark solution is washed with benzene. The aqueous layer is basified with 50% sodium hydroxide and extracted with benzene. The organic extracts are combined, dried over magnesium sulfate and evaporated. The residue is distilled at 170° C. 0.6 torr to give a distillate of the title compound (135.9 g). The title compound is dissolved in diethyl ether and dry hydrogen chloride is added. The precipitate is collected and crystallized from methanol-diethyl ether to obtain the hydrochloride salt of the title compound, mp 212°-214° C.

Provenance & Evidence