US3939202A
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Process for preparing polyene compounds
Assignee: Teikoku Chemical Industry Co Ltd
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Filing: 1974-01-29
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Granted: 1976-02-17
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Expires: 1994-01-29
Abstract
Abstract Polyene compounds of the formula: ##EQU1## wherein R' is protected or unprotected hydroxyl or a group of the formula: ##EQU2## (in which R" and R"' are each carboxyl or a group convertible into carboxyl on hydrolysis), m is a positive integer and n is 0 or a positive integer, which are useful as intermediates in the synthesis of coenzyme Q, can be produced advantageously through a step for the dehydration of a compound of the formula: ##EQU3## wherein R', m and n are each as defined above.
Inventors
- 👤 Masanao Matsui
- 👤 Seiichi Kitamura
- 👤 Masahiro Morioka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:24
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/143; C07C45/00; C07C45/56; C07C45/57; C07C45/58; C07C45/61; C07C45/67; C07C45/68; C07C57/00; C07C57/02; C07C57/03; C07C59/00; C07C59/40; C07C59/76
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
144 words
A process for preparing a polyene compound which comprises: A. reacting a compound of the formula ##EQU12## with a compound of the formula ##EQU13## to form a compound of the formula ##EQU14## B. subjecting the product of (A) to hydrolysis and decarboxylation to form a compound of the formula ##EQU15## C. reducing the product of (B) to form a compound of the formula ##EQU16## D. reacting the product of (C) with a dehydrating agent to form a compound of the formula ##EQU17## where in each occurence above R is a group convertible into carboxyl on hydrolysis, R' is protected or unprotected hydroxyl or a group of the formula ##EQU18## where R" and R'" are each carboxyl or a group convertible into carboxyl on hydrolysis, X is the residue of an acid, m is a positive integer and n is O or a positive integer.
Claim 2
Dependent Claim
144 words
A process for preparing a polyene compound which comprises: A. reacting a compound of the formula ##EQU12## with a compound of the formula ##EQU13## to form a compound of the formula ##EQU14## B. subjecting the product of (A) to hydrolysis and decarboxylation to form a compound of the formula ##EQU15## C. reducing the product of (B) to form a compound of the formula ##EQU16## D. reacting the product of (C) with a dehydrating agent to form a compound of the formula ##EQU17## where in each occurence above R is a group convertible into carboxyl on hydrolysis, R' is protected or unprotected hydroxyl or a group of the formula ##EQU18## where R" and R'" are each carboxyl or a group convertible into carboxyl on hydrolysis, X is the residue of an acid, m is a positive integer and n is O or a positive integer.
Claim 3
Dependent Claim
17 words
A process, as in claim 1, where the reaction (D) is carried out in an inert solvent.
Claim 4
Dependent Claim
38 words
A process, as in claim 1, where by dehydrating agent employed in the reaction (D) is a member selected from the group consisting of phosphorus pentoxide, phosphorus oxychloride, sodium hydrogen sulfite, p-toluenesulfonic acid, sulfuric acid and oxalic acid.
Claim 5
Dependent Claim
29 words
A process, as in claim 1, where the reduction reaction (C) is carried out by treatment with a metal hydride compound or an aluminum alkoxide in an inert solvent.
Claim 6
Dependent Claim
24 words
A process, as in claim 1, where the reaction (A) is carried out in the presence of a basic catalyst in an inert solvent.
Claim 7
Dependent Claim
23 words
A process as in claim 1, where the hydrolysis in (B) is carried out by treatment with a base in an inert solvent.
Claim 8
Dependent Claim
17 words
A process, as in claim 1, where the decarboxylation in (B) is carried out under acidic conditions.
Claim 9
Dependent Claim
97 words
A process, as in claim 1, where the compound reacted in (A) has been formed by: E. reacting a compound of the formula ##EQU19## with a carboxylic acid derivative of the formula RCH 2 X and subjecting the resultant compound to hydrolysis and decarboxylation to form a compound of the formula ##EQU20## F. reacting the product of (E) with a carboxylic acid derivative of the formula RCH 2 X to form a compound of the formula ##EQU21## G. reacting the product of (F) with an oxidizing agent, R, X, and n being defined as in claim 1.
Claim 10
Dependent Claim
35 words
A process as in claim 1, where the compound reacted in (A) has been formed by E. reacting a compound of the formula ##EQU22## where n is defined in claim 1, with a dialkyl carbonate.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-16 | 1979-08-18 | 1980-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-16 | 1983-08-18 | 1984-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-16 | 1987-08-18 | 1988-02-17 | $7700.00 | Window Closed / Lapsed |