Sulfuric Acid → HCID 4550710, compound

Participants

Reaction Steps

Six grams of lithium-aluminum hydride (0.158 mole) was stirred with 200 ml of absolute ether and to this was added dropwise 24.15 g (0.078 mole) of diethyl 1,3-dimethyladamantane-5,7-dicarboxylate in 50 ml of absolute ether at a rate such as to maintain gentle refluxing of the solvent. Refluxing was continued for two hours. Then the excess LiAlH4 was decomposed with moist AcOEt. The reaction mixture was acidified with 20% H2SO4 which gave, by crystallization, 15.3 g of 1,3-dimethyl-5,7-bis (hydroxymethyl)-adamantane (IIb) which was collected by filtration. Another 1.8 g crop was obtained from the filtrate after separating the water phase and evaporating the organic layer. Yield was 17.1 g (97%). MP was 158°-161° C. Recrystallization from ethyl acetate afforded a product MP 160°-162° C.

Provenance & Evidence