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US4031131A
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Process for preparing phenoxybenzoic acids
Assignee: Rohm and Haas Co
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Filing: 1975-09-29
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Granted: 1977-06-21
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Expires: 1995-09-29
Abstract
Abstract Phenoxybenzoic acids and esters of the formula ##STR1## wherein R is hydrogen or alkyl and X is hydrogen or chlorine can be prepared by reacting the disalt of 3-hydroxybenzoic acid with a 3-chloro-4-halobenzotrifluoride. These phenoxybenzoic acids and esters can then be selectively nitrated to give the corresponding 2-nitro-5-(substituted)phenoxybenzoic acids and esters. The nitrated esters can also be prepared by first nitrating the corresponding acid and then esterifying with an appropriate alcohol.
Inventors
- 👤 Wayne O. Johnson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 21:45
CPC Classifications
C; C07; C07C; C07C201/00; C07C201/06; C07C201/08; C07C51/00; C07C51/347; C07C51/353
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
88 words
A method for preparing a compound of the formula ##STR6## wherein X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR7## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, and c. acidifying the product of (b) with a strong inorganic acid.
Claim 2
Independent Claim
88 words
A method for preparing a compound of the formula ##STR6## wherein X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR7## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, and c. acidifying the product of (b) with a strong inorganic acid.
Claim 3
Dependent Claim
13 words
The method of claim 1 wherein X is hydrogen and Y is chlorine.
Claim 4
Independent Claim
112 words
A method for preparing a compound of the formula ##STR8## wherein X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR9## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, c. acidifying the product of (b) with a strong inorganic acid, to form a product of the formula ##STR10## wherein X is as defined above, and d. reacting the product of (c) with a nitrating agent.
Claim 5
Independent Claim
112 words
A method for preparing a compound of the formula ##STR8## wherein X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR9## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, c. acidifying the product of (b) with a strong inorganic acid, to form a product of the formula ##STR10## wherein X is as defined above, and d. reacting the product of (c) with a nitrating agent.
Claim 6
Dependent Claim
13 words
The method of claim 3 wherein X is hydrogen and Y is chlorine.
Claim 7
Independent Claim
166 words
A method for preparing a compound of the formula ##STR11## wherein R is a hydrogen atom or a (C 1 -C 4 ) alkyl group, and X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR12## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, to form a salt of an acid of the formula ##STR13## wherein X is as defined above, c. optionally acidifying the product of (b) with a strong inorganic acid, to form the acid, d. esterifying the salt of (b) or the acid of (c) with a (C 1 -C 4 ) alkanol, e. reacting the product of (d) with a nitrating agent, and f. when R is a hydrogen atom, hydrolyzing the product of (e).
Claim 8
Independent Claim
166 words
A method for preparing a compound of the formula ##STR11## wherein R is a hydrogen atom or a (C 1 -C 4 ) alkyl group, and X is a hydrogen atom or a chlorine atom, which comprises a. reacting 3-hydroxybenzoic acid with at least two equivalents of an inorganic base to form the disalt of the 3-hydroxybenzoic acid, b. reacting in a polar aprotic organic solvent the disalt with a benzotrifluoride of the formula ##STR12## wherein Y is a chlorine atom or a fluorine atom and X is as defined above, to form a salt of an acid of the formula ##STR13## wherein X is as defined above, c. optionally acidifying the product of (b) with a strong inorganic acid, to form the acid, d. esterifying the salt of (b) or the acid of (c) with a (C 1 -C 4 ) alkanol, e. reacting the product of (d) with a nitrating agent, and f. when R is a hydrogen atom, hydrolyzing the product of (e).
Claim 9
Dependent Claim
13 words
The method of claim 5 wherein X is hydrogen and Y is chlorine.
Claim 10
Dependent Claim
16 words
The method of claim 6 wherein R is a (C 1 -C 4 ) alkyl group.
Claim 11
Dependent Claim
20 words
The method of claim 7 wherein the acid of (c) is esterified with a (C 1 -C 4 ) alkanol.
Claim 12
Dependent Claim
11 words
The method of claim 6 wherein R is a hydrogen atom.
Claim 13
Independent Claim
60 words
A method for preparing a salt of a compound of the formula ##STR14## wherein X is a hydrogen atom or a chlorine atom, which comprises reacting in a polar aprotic organic solvent a disalt of 3-hydroxybenzoic acid with a benzotrifluoride of the formula ##STR15## wherein Y is a chlorine atom or a fluorine atom, and X is as defined above.
Claim 14
Independent Claim
60 words
A method for preparing a salt of a compound of the formula ##STR14## wherein X is a hydrogen atom or a chlorine atom, which comprises reacting in a polar aprotic organic solvent a disalt of 3-hydroxybenzoic acid with a benzotrifluoride of the formula ##STR15## wherein Y is a chlorine atom or a fluorine atom, and X is as defined above.
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) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |