Process for synthesis of coenzyme Q compounds

Details Process for synthesis of coenzyme Q compounds Process for synthesis of coenzyme Q compounds

1976-09-22

1977-12-06

Garner, Vivian

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260462C, 260613D, C07C 4973, C07F 504

Patent

active

040616606

ABSTRACT:
A process for the synthesis of 2,3-dimethoxy-5-methyl-6-substituted-1,4-benzoquinones having the formula: ##STR1## wherein R is ##STR2## in which n is an integer of 0 to 9, and A and B are hydrogens or A--B is a direct valence bond between the carbon atoms to which they are attached,
Characterized by reacting 2-methyl-4,5,6-trimethoxyphenol with an aryl boronic acid, a lower alkyl boronic acid or an acid anhydride thereof to obtain a 2-methyl-4,5,6-trimethoxyphenol ester of boric acid, reacting the resulting ester with an n-prenol or iso-prenol having the formula: ##STR3## wherein R is as defined above, OR A REACTIVE DERIVATIVE OF SAID N- OR ISO-PRENOL, IN THE PRESENCE OF A SILICA-ALUMINA COMPOUND, TO OBTAIN A 2-METHYL-3-SUBSTITUTED-4,5,6-TRIMETHOXYPHENOL ESTER OF BORIC ACID, AND HYDROLYZING THE THUS-OBTAINED ESTER AND TREATING THE RESULTING 2-METHYL-3-SUBSTITUTED-4,5,6-TRIMETHOXYPHENOL HAVING THE FORMULA: ##STR4## wherein R is as defined above, WITH AN OXIDIZING AGENT.

REFERENCES:
patent: 3896153 (1975-07-01), Sato et al.

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