US4062879A
Expired / Lapsed
US
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Process for synthesis of coenzyme Q compounds
Assignee: Eisai Co Ltd
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Filing: 1976-09-22
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Granted: 1977-12-13
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Expires: 1996-09-22
Abstract
Abstract A process for synthesizing 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 taken together form a valence bond, In which 2-methyl-4,5,6-trimethoxyphenol is reacted with boric acid or a reactive derivative 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 oxidant.
Inventors
- 👤 Shizumasa Kijima
- 👤 Isao Yamatsu
- 👤 Norio Minami
- 👤 Yuichi Inai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 23:57
CPC Classifications
C; C07; C07F; C07F5/00; C07F5/02; C07F5/04; C07C; C07C46/00; C07C46/02; C07C46/06; C07C50/00; C07C50/26; C07C50/28
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
47 words
A process for synthesizing 2,3-dimethoxy-5-methyl-6-substituted-1,4-benzoquinone having the formula ##STR10## wherein R is ##STR11## in which n is an integer from zero 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, which comprises
Claim 2
Dependent Claim
47 words
A process for synthesizing 2,3-dimethoxy-5-methyl-6-substituted-1,4-benzoquinone having the formula ##STR10## wherein R is ##STR11## in which n is an integer from zero 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, which comprises
Claim 3
Dependent Claim
75 words
reacting 2-methyl-4,5,6-trimethoxyphenol with a member selected from the group consisting of borax, boric anhydride, orthoboric acid and metaboric acid to form the corresponding borate, 2. reacting the borate obtained in step (1 ) with a prenol compound having the formula ##STR12## an iso-prenol compound having the formula ##STR13## wherein R has the same meaning as defined above, or a corresponding halide derivative thereof, in the presence of a silica-alumina compound, to obtain the 2-methyl-3-substituted-4,5,6-trimethoxyphenyl borate,
Claim 4
Dependent Claim
75 words
reacting 2-methyl-4,5,6-trimethoxyphenol with a member selected from the group consisting of borax, boric anhydride, orthoboric acid and metaboric acid to form the corresponding borate, 2. reacting the borate obtained in step (1 ) with a prenol compound having the formula ##STR12## an iso-prenol compound having the formula ##STR13## wherein R has the same meaning as defined above, or a corresponding halide derivative thereof, in the presence of a silica-alumina compound, to obtain the 2-methyl-3-substituted-4,5,6-trimethoxyphenyl borate,
Claim 5
Dependent Claim
43 words
hydrolyzing the borate obtained in step (2) to obtain a compound having the formula ##STR14## wherein R has the same meaning as defined above and then reacting the latter compound with a mild oxidizing agent to obtain a compound of the first-named formula.
Claim 6
Dependent Claim
43 words
hydrolyzing the borate obtained in step (2) to obtain a compound having the formula ##STR14## wherein R has the same meaning as defined above and then reacting the latter compound with a mild oxidizing agent to obtain a compound of the first-named formula.
Claim 7
Dependent Claim
44 words
A process as claimed in claim 1 in which said prenol compound or said isoprenol compound is selected from the group consisting of 3-methylbuten-2-ol-1, 3-methylbuten-1-ol-3, geraniol, linalool, nerol, nerolidol, phytol, isophytol, geranylgeraniol, geranyllinalool, geranylfarnesol, geranylnerolidol, farnesylfarnesol, farnesylnerolidol, geranylgeranylfarnesol, solanesol, decaprenol, isodecaprenol, and halides thereof.
Claim 8
Dependent Claim
31 words
A process as claimed in claim 1 in which said silica-alumina compound is selected from the group consisting of clay, active clay, kaolin, natural and synthetic zeolites, silica-alumina, silica-alumina-boria and silia-alumina-magnesia.
Claim 9
Dependent Claim
32 words
A process as claimed in claim 1 in which said mild oxidizing agent is selected from the group consisting of silver oxide, lead oxide, ferric chloride, aqueous hydrogen peroxide and mixtures thereof.
Claim 10
Dependent Claim
45 words
A process for synthesizing borates of ##STR15## wherein R is ##STR16## in which n is an integer from zero 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. which comprises
Claim 11
Dependent Claim
45 words
A process for synthesizing borates of ##STR15## wherein R is ##STR16## in which n is an integer from zero 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. which comprises
Claim 12
Dependent Claim
76 words
reacting 2-methyl-4,5,6-trimethoxyphenol with a member selected from the group consisting of borax, boric anhydride, othoboric acid and metaboric acid to form the corresponding borate, and 2. reacting the borate obtaining in step (1) with a prenol compound having the formula ##STR17## or an iso-prenol compound having the formula ##STR18## wherein R has the same meaning as defined above, or a corresponding halide derivative thereof in the presence of a silica-alumina compound to obtain the 2-methyl-3-substituted-4,5,6-trimethoxyphenyl borate.
Claim 13
Dependent Claim
76 words
reacting 2-methyl-4,5,6-trimethoxyphenol with a member selected from the group consisting of borax, boric anhydride, othoboric acid and metaboric acid to form the corresponding borate, and 2. reacting the borate obtaining in step (1) with a prenol compound having the formula ##STR17## or an iso-prenol compound having the formula ##STR18## wherein R has the same meaning as defined above, or a corresponding halide derivative thereof in the presence of a silica-alumina compound to obtain the 2-methyl-3-substituted-4,5,6-trimethoxyphenyl borate.
Claim 14
Dependent Claim
44 words
A process as claimed in claim 5 in which said prenol compound or said isoprenol compound is selected from the group consisting of 3-methylbuten-2-ol-1, 3-methylbuten-1-ol-3, geraniol, linalool, nerol, nerolidol, phytol, isophytol, geranylgeraniol, geranyllinalool, geranylfarnesol, geranylnerolidol, farnesylfarnesol, farnesylnerolidol, geranylgeranylfarnesol, solanesol, decaprenol, isodecaprenol, and halides thereof.
Claim 15
Dependent Claim
31 words
A process as claimed in claim 5 in which said silica-alumina compound is selected from the group consisting of clay, active clay, kaolin, natural and synthetic zeolites, silica-alumina silica-alumina-boria and silica-alumina-magnesia.
References Cited (Backward Citations)
US3068295A
Cited
US3896153A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |