US3954876A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of halo-substituted derivatives of acetophenone
Assignee: Yeda Research and Development Co Ltd
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Filing: 1974-11-04
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Granted: 1976-05-04
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Expires: 1994-11-04
Abstract
Abstract A process for producing halosubstituted derivatives of acetophenone from the respective halocumenes, the term "halo" as used herein, signifying chlorine or bromine, the molecule containing 1 to 3 nuclear halo substituents in the meta- and/or paraposition relative to the isopropyl group. The process comprises oxidizing the halocumene by means of air or oxygen. The oxidation is effected in the presence of a metal phthalocyanine complex as catalyst, and in a most preferred embodiment, in the co-presence of a dichlorobenzene solvent. The preferred halocumenes are p-chlorocumene and p-bromocumene.
Inventors
- 👤 David Vofsi
- 👤 Jonathan Freddy Cohen
- 👤 Michael Martan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 08:34
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27; C07C45/32; C07C45/33; C07C45/34; C07C45/36
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
96 words
A process for the preparation of a haloacetophenone of the formula ##SPC1## wherein X is chloro or bromo and n is 1-3, the halo substituents being meta and/or para to the ##EQU1## group, said process comprising oxidizing a halocumene of the formula: ##SPC2## wherein X and n are as defined above at a temperature between 130°C. and 160°C. with air or oxygen, and in the presence of a catalytically effective amount of a metal phthalocyanine selected from the group consisting of iron, copper and cobalt phthalocyanine and in the presence of a dichlorobenzene as a solvent.
Claim 2
Dependent Claim
96 words
A process for the preparation of a haloacetophenone of the formula ##SPC1## wherein X is chloro or bromo and n is 1-3, the halo substituents being meta and/or para to the ##EQU1## group, said process comprising oxidizing a halocumene of the formula: ##SPC2## wherein X and n are as defined above at a temperature between 130°C. and 160°C. with air or oxygen, and in the presence of a catalytically effective amount of a metal phthalocyanine selected from the group consisting of iron, copper and cobalt phthalocyanine and in the presence of a dichlorobenzene as a solvent.
Claim 3
Dependent Claim
12 words
The process of claim 1, wherein said metal phthalocyanine is copper phthalocyanine.
Claim 4
Dependent Claim
17 words
The process of claim 1, wherein oxidation is effected at a pressure between 0.2 and 50 atm.
Claim 5
Dependent Claim
19 words
The process of claim 1, wherein n is 1 and the halo substituents are para to the keto group.
Claim 6
Dependent Claim
22 words
The process of claim 1, wherein the halocumene and the dichlorobenzene are present in a weight ratio of about 0.5 to 1.0.
Claim 7
Dependent Claim
10 words
The process of claim 1, wherein the dichlorobenzene is o-dichlorobenzene.
Claim 8
Dependent Claim
19 words
The process of claim 1, wherein the amount of catalyst is about 0.1% by weight based on the halocumene.
Claim 9
Dependent Claim
17 words
The process of claim 1, wherein the reaction is run for from about 2 to 4 hours.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-04 | 1979-11-03 | 1980-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-04 | 1983-11-03 | 1984-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-04 | 1987-11-03 | 1988-05-04 | $7700.00 | Window Closed / Lapsed |