39068-88-7Relevant articles and documents
Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide
Zalomaeva, Olga V.,Evtushok, Vasilii Yu.,Maksimov, Gennadii M.,Maksimovskaya, Raisa I.,Kholdeeva, Oxana A.
, p. 5202 - 5209 (2017/04/27)
The selective oxidation of methoxy/methyl-substituted arenes to the corresponding benzoquinones has been first realized using aqueous hydrogen peroxide as a green oxidant, acid tetrabutylammonium salts of the γ-Keggin divanadium-substituted phosphotungstate [γ-PW10O38V2(μ-O)2]5- (I) as a catalyst, and MeCN as a solvent. The presence of the dioxovanadium core in the catalyst is crucial for the catalytic performance. The reaction requires an acid co-catalyst or, alternatively, a highly protonated form of I can be prepared and employed. The industrially relevant oxidation of 3,4,5-trimethoxytoluene gives 2,3-dimethoxy-5-methyl-1,4-benzoquinone (ubiquinone 0 or coenzyme Q0, the key intermediate for coenzyme Q10 and other essential biologically active compounds) with 73% selectivity at 76% arene conversion. The catalyst retains its structure under turnover conditions and can be easily recycled and reused without significant loss of activity and selectivity.
Synthesis of coenzyme Q10
Oh, Eun-Taek,Taek Oh, Jung,Koo, Sangho,Jin Kim, Hee,Su, Liang,Yun, Inkyun,Nam, Kyunggu,Min, Jae-Hong,Woo Kim, Joon
, p. 4954 - 4962,9 (2020/08/24)
A practical synthesis of coenzyme Q10 has been developed. The route features an improved Friedel-Crafts allylation of tetramethoxytoluene with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride at 40 °C. Replacement of the methyl ether protecting groups of the para-hydroquinone by methoxymethyl groups at Q1 stage proceeded efficiently, and allowed the facile final oxidation to coenzyme Q10 to occur under mild acidic conditions. The overall yield of coenzyme Q 10 from commercially available tetramethoxytoluene reached 53 % in this improved procedure. An improved synthesis gave CoQ10 in 53 % overall yield from tetramethoxytoluene through Friedel-Crafts allylation with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride and a modified oxidation procedure. Copyright
An alternative route for the synthesis of 2,3,4,5-tetramethoxytoluene
Vera, William J.,Chinea, Kimberly,Banerjee, Ajoy K.
experimental part, p. 186 - 187 (2009/10/15)
The transformation of the commercially available 2,3,4- trimetho×ybenzaldehyde to 2,3,4,5-tetrametho×ytoluene using a Dakin reaction to insert the extra oxygen, formylation, reduction and methylation of the phenolic hydro×yl group is described.
