Geranylacetone → 6,10-Dimethyl-2-undecanol

Participants

Reaction Conditions

Reaction Steps

To a glass autoclave liner is added 299 g of geranylacetone, 3.8 g or 5% ruthenium on carbon and 150 ml of methanol. The glass liner is sealed inside a 3 L, stainless steel, rocking autoclave and the autoclave purged once with 250 psig N2, once with 250 psig H2 and then charged with 1000 psig H2. With mixing, the reaction mixture is heated. At about 75° C., the reaction initiates and begins consuming H2 and exotherms to 170-180° C. In 10-15 minutes, the temperature has dropped to 100-110° C. and the pressure dropped to 500 psig. The autoclave is boosted to 1000 psig with H2 and mixed at 100-110° C. for an additional 1 hour and 40 minutes with the reaction consuming an additional 160 psig H2 but at which time no more H2 consumption is observed. Upon cooling the autoclave to 40° C., the reaction mixture removed, filtered to remove catalyst and concentrated by evaporation of methanol under vacuum to yield 297.75 g of 6,10-dimethyl-2-undecanol.

Provenance & Evidence