Hydrochloric Acid → 2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octane

Participants

Reaction Conditions

Reaction Steps

2-(5-Methoxyhept-1-y)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (5 g, 19.8 mmoles) is mixed with diethylene glycol (27 ml) and potassium hydroxide (3.8 g, 6.7 mmoles). The reaction is stirred and mixed with 80% hydrazine hydrate (2.8 ml, 7.0 mmoles). The reaction is heated to 95° C. for 2 hours. After which time the temperature is increased to 200° C. and maintained with stirring for 5 hours. Then the reaction is cooled and added to 6N hydrochloric acid (200 ml). The solution is partitioned between ether and the phases separated. The aqueous phase is extracted with ether (2×100 ml) and the extracts combined. The ether solution is dried over anhydrous magnesium sulfate and the solvent removed under vacuum leaving a clear, purple oil. The crude product is kugelrohred under reduced pressure leaving a clear, colorless oil (4.0 g, 16.8 mmoles).

Provenance & Evidence