US3852359A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-(sulfur-substituted)-3-hydroxy-5,3-dimethyl-2-cyclohexen-1-ones and preparation
Assignee: Dow Chemical Co
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Filing: 1972-12-29
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Granted: 1974-12-03
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Expires: 1992-12-29
Abstract
Abstract WHEREIN R1 is a 1 to 6 carbon atom alkyl, benzyl, halobenzyl, lower alkylbenzyl, nitrobenzyl, alkenyl, haloalkenyl, 2-(lower alkylthio)lower alkyl or cyclohexylmethyl group, R2 is hydrogen, ammonium or alkali metal and n is an integer from 0 to 2. The compounds are prepared by reacting an alkali metal salt of 3hydroxy-5,5-dimethyl-2-cyclohexen-1-one with a thiosulfonate. The compounds are useful as plant growth regulators. Concerns compounds of the formula
Inventors
- 👤 J Dunbar
- 👤 T Bohnert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:52
CPC Classifications
C; C07; C07C; C07C323/00; C07C317/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
6 words
A 2-(SULFUR-SUBSTITUTED)-3-HYDROXY-5-DIMETHYL-2CYCLOHEXEN-1-ONE CORRESPONDING TO THE FORMULA
Claim 2
Dependent Claim
6 words
A 2-(SULFUR-SUBSTITUTED)-3-HYDROXY-5-DIMETHYL-2CYCLOHEXEN-1-ONE CORRESPONDING TO THE FORMULA
Claim 3
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-chlorobenzylthio)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 4
Dependent Claim
8 words
The compound of claim 1 whIch is 2-(p-chlorobenzylsulfinyl)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is 2-((p-chlorobenzyl)sulfonyl)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-fluorobenzylthio)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-fluorobenzylsulfinyl)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 3-hydroxy-5,5-dimethyl-2-(p-methylbenzylthio)-2-cyclohexen-1-one.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 3-hydroxy-5,5-dimethyl-2-(p-methylbenzylsulfinyl)-2-cyclohexen-1-one.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 2-benzylthio-3-hydroxy-2,2-dimethyl-2-cyclohexen-1-one.
Claim 11
Dependent Claim
8 words
The compound of claim 1 which is 2-benzylsulfinyl-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 12
Dependent Claim
8 words
The compound of claim 1 which is 2-benzylsulfonyl-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one.
Claim 13
Dependent Claim
10 words
A process for making a 3-hydroxy-2-mercapto-5,5-dimethyl-2-cyclohexen-1-one corresponding to the formula
Claim 14
Dependent Claim
10 words
A process for making a 3-hydroxy-2-mercapto-5,5-dimethyl-2-cyclohexen-1-one corresponding to the formula
Claim 15
Dependent Claim
50 words
The process of claim 12 also including the steps of mixing the product 2-mercapto-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one with a substantially equimolar proportion of hydrogen peroxide in glacial acetic acid as reaction medium and allowing the oxidation to proceed to form the corresponding sulfinyl derivative, and recovering the sulfinyl derivative from the reaction medium.
Claim 16
Dependent Claim
49 words
The process of claim 12 also including the steps of mixing the 2-mercapto-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one with substantially 2 molar proportions of hydrogen peroxide in the presence of glacial acetic acid as reaction medium at a temperature between about 30* and 100*C. and recovering the corresponding sulfonyl derivative from the reaction medium.
Claim 17
Dependent Claim
42 words
The process of claim 13 also including the step of mixing the 2-sulfinyl derivative with substantially one molar proportion of hydrogen peroxide in the presence of glacial acetic acid as reation medium and recovering the corresponding 2-sulfonyl-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one product from the reaction medium.
References Cited (Backward Citations)
US3345402A
Cited
US3387034A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-02 | 1978-06-03 | 1978-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-02 | 1982-06-03 | 1982-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-02 | 1986-06-03 | 1986-12-03 | $7700.00 | Window Closed / Lapsed |