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US4225731A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of trifluoromethylphenols

Assignee: Bayer AG
•
Filing: 1978-07-13
•
Granted: 1980-09-30
•
Expires: 1998-07-13
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Abstract

Abstract A process for the preparation of a trifluoromethylphenol or the corresponding alkoxy compound which comprises contacting a halogenobenzotrifluoride of the formula ##STR1## in which X denotes halogen, R 1 , R 2 and R 3 denote hydrogen, trifluoromethyl or a substituent which promotes the replacement of X by a hydroxyl group and Y denotes hydrogen, a halogen or alkoxy, at least one of the substituents R 1 , R 2 and R 3 representing a trifluoromethyl group and at least one of them representing a substituent which promotes the replacement of the radical X by a hydroxyl group, with an excess aqueous alkali metal hydroxide in an alcoholic solution in the presence of a quaternary onium salt.

Inventors

  • 👤 Albrecht Marhold
  • 👤 Erich Klauke

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 00:02
CPC Classifications
C; C07; C07C; C07C201/00; C07C201/06; C07C201/12

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 214 words
A process for the preparation of a trifluoromethylphenol or the corresponding alkoxy compound which comprises contacting a halogenobenzotrifluoride of the formula ##STR10## in which X denotes halogen, R 1 , R 2 and R 3 denote hydrogen, trifluoromethyl or a substituent which promotes the replacement of X by a hydroxyl group and Y denotes hydrogen, halogen or alkoxy, at least one of the substituents R 1 , R 2 and R 3 representing a trifluoromethyl group and at least one of them representing a substituent which promotes the replacement of the radical X by a hydroxl group, with an excess aqueous alkali metal hydroxide in an alcoholic solution in the presence of a quaternary onium salt of the formula ##STR11## in which Z denotes an atom of main group 5 of the periodic system, R 4 to R 7 independently of one another denote alkyl , substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, or substituted aryl, of two of the radicals R 4 to R 7 , together with the central atom Z which can additionally contain additional hetero-atoms, form a heterocyclic ring, the radicals R 4 to R 7 together containing at least 6 carbon atoms, and A denotes a chloride, bromide or hydroxide anion, at a temperature of from 0° to 80° C.
Claim 2
Dependent Claim 214 words
A process for the preparation of a trifluoromethylphenol or the corresponding alkoxy compound which comprises contacting a halogenobenzotrifluoride of the formula ##STR10## in which X denotes halogen, R 1 , R 2 and R 3 denote hydrogen, trifluoromethyl or a substituent which promotes the replacement of X by a hydroxyl group and Y denotes hydrogen, halogen or alkoxy, at least one of the substituents R 1 , R 2 and R 3 representing a trifluoromethyl group and at least one of them representing a substituent which promotes the replacement of the radical X by a hydroxl group, with an excess aqueous alkali metal hydroxide in an alcoholic solution in the presence of a quaternary onium salt of the formula ##STR11## in which Z denotes an atom of main group 5 of the periodic system, R 4 to R 7 independently of one another denote alkyl , substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, or substituted aryl, of two of the radicals R 4 to R 7 , together with the central atom Z which can additionally contain additional hetero-atoms, form a heterocyclic ring, the radicals R 4 to R 7 together containing at least 6 carbon atoms, and A denotes a chloride, bromide or hydroxide anion, at a temperature of from 0° to 80° C.
Claim 3
Dependent Claim 31 words
A process according to claim 1 wherein the quaternary onium saltis an quaternary ammonium or quaternary phosphonium salt, the substituents of which contain a total of 8 to 25 carbon atoms.
Claim 4
Dependent Claim 47 words
A process according to claim 1 wherein the quaternary onium salt is a quaternary ammonium salt and the quaternary ammonium salt is an ion exchanger which is based on styrene with 2 mol percent of divinylbenzene as cross-linking agent and the ion exchanger contain quaternary ammonium groups.
Claim 5
Dependent Claim 29 words
A process according to claim 1 wherein the quaternary onium salt is employed in an amount of 1 to 20% by weight based upon the weight of the halogenobenzotrifluoride.
Claim 6
Dependent Claim 29 words
A process according to claim 4 wherein the quaternary onium salt is employed in an amount of 5 to 10% by weight based upon the weight of the halogenobenzotrifluoride.
Claim 7
Dependent Claim 17 words
A process according to claim 1 wherein the alcoholic solvent is a lower unbranched or branched alkanol.
Claim 8
Dependent Claim 35 words
A process according to claim 1 wherein the alkali metal hydroxide is employed in at least about three times the molar amount based on the reaction of halogen atom to give the phenolic hydroxyl group.
Claim 9
Dependent Claim 30 words
A process according to claim 1 wherein the reaction is carried out at a temperature in the range of 15° to 35° C. whereby the corresponding alkoxy compound is formed.
Claim 10
Dependent Claim 23 words
A process according to claim 1 wherein the reaction is carried out at a temperature in the range of 50° to 75° C.
Claim 11
Dependent Claim 38 words
A process according to claim 1 wherein as a result of said reaction there is formed the corresponding alkali metal salt and alkali metal salt is converted to the corresponding phenol by contacting the same with an acid.
Claim 12
Dependent Claim 105 words
A process according to claim 1 wherein R 4 to R 7 independently of one another denote C 1 to C 18 alkyl, substituted C 1 -C 18 alkyl, cyclopentyl or cyclohexyl, C 1 -C 4 -alkyl substituted cyclopentyl or cyclohexyl, phenyl, C 1 -C 4 -alkyl, methoxy, ethoxy or halo substituted phenol or two of the radicals R 4 to R 7 , together with the central atom Z to form a heterocyclic ring selected from the group consisting of the pyrrolidine ring, the piperidine ring or the morpholine ring, the radicals R 4 to R 7 together containing at least 6 carbon atoms.

References Cited (Backward Citations)

GB718779A Cited
US2872461A Cited
US2950325A Cited
US3351670A Cited
FR1469596A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-30 1984-03-31 1984-09-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-30 1988-03-31 1988-09-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-30 1992-03-31 1992-09-30 $7700.00 Window Closed / Lapsed

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