Water → 5,9,13-Pentadecatrien-2-ol, 6,10,14-trimethyl-, (5E,9E)-

Participants

Reaction Conditions

Reaction Steps

To a 3 liter three-neck flask equipped with a dropping funnel, a stirrer and a condenser were added 38 g of lithium aluminum hydride and 700 ml of ethyl ether in a nitrogen gas stream and the mixture was stirred while maintaining at 0 ° C. To this solution was added dropwise 262 g (1.0 mol) of compound (6) as obtained above dissolved in 500 ml of ethyl ether within about 1 hour and the mixture was further reacted under stirring at room temperature for about 13 hours. After the completion of the reaction, 380 ml of water and 380 ml of a 15% aqueous solution of sodium hydroxide were added to the reaction mixture. The white crystals thus formed were separated by filtering through 50 g of Celite, extracted with 500 ml of ethyl ether three times and then concentrated after dehydrating with sodium sulfate anhydride. 251 g of the oily substance thus obtained was purified by silica gel column chromatography (silica gel: 1000 g, developing solvent: hexane:ethyl acetate=2:1 by volume). Thus 250 g (yield: 94.7 %) of the target 6,10,14- trimethyl-5,9,13-pentadecatrien-2-ol, compound (3), was obtained.

Provenance & Evidence