Coenzyme Q <sub> 10 </ Sub> Synthesis And Optimization

Coenzyme Q₁0 is an important pharmaceutical. A commercial and practical synthesis route with solanesol and 6-(3'-methyl-4'-phenylsulfonylbut-2'-enyl)-2,3 -dimethoxy-5-methylhydroquinone-O,O'-dibenzyl ether(l) as materials is studied. Coenzyme Q₁0 is synthesized by coupling reaction between a sulfonyl component 1) and solanesyl bromide and Benkerser's reductive elimnation of the sulfon-e group followed by oxidation of the resulting hydroquinone.The optimized conditions of the first reaction are: the mole ratio of solanesol to catalyst C to PBr3 equals tol:0.3:l, reaction temperature is -10°C, droping time is 60 minutes. The yield is 96.04%. The optimized conditions of the second reaction are: the mole ratio of solanesyl bromide to 1 to base F is 1:1:2, reaction temperature is -20°C, reaction time is 40 minutes. The yield of compound 2 in this step is 69.3% and the purity is 63.4%. The optimized conditions of the third reaction are: the mole ratio of 2 to lithium to amine is 1:23:467, reaction temperature is-80°C, dropping time is 3minutes. Then the product is exposed to air for 10 minutes to have the resulting hydroquinone oxidized to coenzyme Q₁0.The yield of the these two steps is 77.9% and the purity is 64.7%. The product is recrystallized and the purity reaches to 94.86%.