US4012428A
Expired / Lapsed
US
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Method for preparing 3-methyl-2-(4-halogenophenyl)-butyronitrile
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1975-11-26
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Granted: 1977-03-15
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Expires: 1995-11-26
Abstract
Abstract A method for preparing a 3-methyl-2-(4'-halogenophenyl)-butyronitrile which comprises alkylating a p-halogenophenylacetonitrile by reacting the p-halogenophenylacetonitrile with an isopropyl halide in the presence of an aqueous alkali metal hydroxide solution, using an organic guaternary ammonium salt as a catalyst.
Inventors
- 👤 Nobuo Ohno
- 👤 Takeaki Umemura
- 👤 Tetsuhiko Watanabe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:26
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/01; C07C255/32
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
119 words
A method for preparing a 3-methyl-2-(4'halogenophenyl)-butyronitrile which comprises isopropylating, at a temperature between room temperature and 120° C, a p-halogenophenylacetonitrile with an isopropyl halide in the presence of an organic quaternary ammonium salt selected from the group consisting of triethylbenzylammonium chloride, triethylbenzylammonium bromide, triethylbenzylammonium iodide, triethylbenzylammonium hydroxide, trimethylbenzylammonium chloride, trimethylbenzylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, 3-phenoxybenzyl-triethylammonium bromide, tripropylbenzylammonium chloride, triethylpropylammonium bromide, cetyltriethylammonium bromide, m-octyltrimethylammonium chloride, and p-methoxybenzyltriethylammonium chloride, as a catalyst, and in the presence of an aqueous alkali metal hydroxide solution, wherein said ammonium salt catalyst is present in an amount of from 1/200 to 1/5 mole per mole of the phenylacetonitrile, and wherein the concentration of said alkali metal hydroxide solution is 10 to 70% by weight.
Claim 2
Independent Claim
119 words
A method for preparing a 3-methyl-2-(4'halogenophenyl)-butyronitrile which comprises isopropylating, at a temperature between room temperature and 120° C, a p-halogenophenylacetonitrile with an isopropyl halide in the presence of an organic quaternary ammonium salt selected from the group consisting of triethylbenzylammonium chloride, triethylbenzylammonium bromide, triethylbenzylammonium iodide, triethylbenzylammonium hydroxide, trimethylbenzylammonium chloride, trimethylbenzylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, 3-phenoxybenzyl-triethylammonium bromide, tripropylbenzylammonium chloride, triethylpropylammonium bromide, cetyltriethylammonium bromide, m-octyltrimethylammonium chloride, and p-methoxybenzyltriethylammonium chloride, as a catalyst, and in the presence of an aqueous alkali metal hydroxide solution, wherein said ammonium salt catalyst is present in an amount of from 1/200 to 1/5 mole per mole of the phenylacetonitrile, and wherein the concentration of said alkali metal hydroxide solution is 10 to 70% by weight.
Claim 3
Dependent Claim
21 words
The method according to claim 1, wherein the concentration of the alkali metal hydroxide solution is 40% to 60%, by weight.
Claim 4
Dependent Claim
21 words
The method according to claim 1, wherein the reaction is carried out at a temperature ranging from 45° to 60° C.
Claim 5
Dependent Claim
31 words
The method according to claim 1 wherein the amount of said aqueous metal hydroxide solution in the reaction system ranges from about 1 to 15 times the weight of the reactants.
References Cited (Backward Citations)
US3413309A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-14 | 1980-09-13 | 1981-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-14 | 1984-09-13 | 1985-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-14 | 1988-09-13 | 1989-03-15 | $7700.00 | Window Closed / Lapsed |