Hydrochloric Acid → HCID 14555670, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 66 gm 9(3-methylphenyl)-7-ketononanoic acid in 35 ml diethylene glycol was added 4.3 ml hydrazine hydrate. The reaction mixture was heated at 120° for 5 hrs, cooled to 70° C., connected to a water aspirator, and re-heated to 120°-30° for 31/2 hrs. The mixture was then cooled to 70°, 6.5 g KOH was added, and the reaction mixture was heated to 160°-200° (temperature varied with N2 evolution) for 11 hr, then cooled to room temperature. The solidified reaction mass was dissolved in 150 ml hot water, acidified with conc. HCl, three times extracted with CHCl3 and the organic phases were combined. They were washed three times with water, once with saturated NaCl solution, dried over MgSO4, filtered, treated with charcoal, filtered through diatomaceous earth, and the solvent was removed in vacuo to give a brown oil which was vacuum distilled. Yield 61%. The main fraction boiled at 170°-80° at 0.1 mm and later solidified to a product of m.p. 39°-40°. Elemental analysis: calculated C 77.37, H 9.74. Found: C 77.25, H 9.98.

Provenance & Evidence