Potassium Hydroxide → Bicyclo[2.2.2]octane, 1-methoxy-

Participants

Reaction Conditions

Reaction Steps

To a solution of potassium hydroxide (17 g, 250 mmol) and 85% hydrazine hydrate (11.5 g, 186 mmol) in ethylene glycol (220 mL) was added 1-methoxybicyclo[2.2.2]octan-2-one (11.0 g, 71.4 mmol). The mixture was heated to 195° C. over 1 h and heated for an additional hour. The flask was then fitted for distillation, and approximate 20 mL (two layers) of liquid was collected over a period of 1 h at 195° C. Subsequent dropwise addition of water (215 mL) to the reaction over a period of 3 h afforded a second fraction of distillates (approximately 180 mL). The combined distillates were extracted with ether (3×80 mL), the organic phase was dried over Na2SO4, and the volatiles were removed to produce 1-methoxybicyclo[2.2.2]octane (4.5 g, 45%) which was used in the next step directly without purification. 1H NMR (CDCl3, 400 MHz) δ 3.14 (s, 3H), 1.63-1.59 (m, 6H), 1.58-1.51 (m, 6H), 1.47 (m, 1H).

Provenance & Evidence