US4489013A
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US
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Preparation of α-oxo-α-(3-alkoxycarbonyl-2,2-dimethyl-cycloprop-1-yl)-methane-phosphonic acid esters
Assignee: Bayer AG
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Filing: 1983-10-07
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Granted: 1984-12-18
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Expires: 2003-10-07
Abstract
Abstract A process for the preparation of an α-oxo-α-(3-alkoxycarbonyl-2,2-dimethyl-cycloprop-1-yl)-methane-phosphonic acid ester of the formula ##STR1## in which R is alkyl or a radical customary in the alcohol component of pyrethroids, and R 1 is alkyl or phenyl, or the two radicals R 1 together are alkanediyl, comprising reacting β,β-dimethyl-acrylic acid chloride of the formula ##STR2## with a phosphorous acid ester of the formula R.sup.4 O--P(OR.sup.1).sub.2 in which R 4 is alkyl, at a temperature between about 0° and 100° C., to produce the novel compound 1-oxo-3-methyl-2-butene-phosphonic acid of the formula ##STR3## which is then reacted with a sulphuranylidene-acetic acid ester of the formula ##STR4## in which R 2 and R 3 each independently is alkyl or together are alkanediyl, at a temperature between about 0° and 100° C.
Inventors
- 👤 Hellmut Hoffmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 20:39
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4062; C07F9/4065; C07D; C07D333/00; C07D333/02; C07D333/46
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
88 words
A process for the preparation of an α-oxo-α-(3-alkoxycarbonyl-2,2-dimethyl-cycloprop-1-yl)-methane-phosphonic acid ester of the formula ##STR15## in which R is alkyl or a radical customary in the alcohol component of pyrethroids, and R 1 is alkyl or phenyl, or the two radicals R 1 together are alkanediyl, comprising reacting a 1-oxo-3-methyl-2-butene-phosphonic acid ester of the formula ##STR16## with a sulphuranylidene-acetic acid ester of the formula ##STR17## in which R 2 and R 3 each independently is alkyl or together are alkanediyl, at a temperature between about 0° and 100° C.
Claim 2
Dependent Claim
88 words
A process for the preparation of an α-oxo-α-(3-alkoxycarbonyl-2,2-dimethyl-cycloprop-1-yl)-methane-phosphonic acid ester of the formula ##STR15## in which R is alkyl or a radical customary in the alcohol component of pyrethroids, and R 1 is alkyl or phenyl, or the two radicals R 1 together are alkanediyl, comprising reacting a 1-oxo-3-methyl-2-butene-phosphonic acid ester of the formula ##STR16## with a sulphuranylidene-acetic acid ester of the formula ##STR17## in which R 2 and R 3 each independently is alkyl or together are alkanediyl, at a temperature between about 0° and 100° C.
Claim 3
Dependent Claim
16 words
A process according to claim 1, wherein the reaction is effected in an inert organic solvent.
Claim 4
Dependent Claim
20 words
A process according to claim 1, wherein the reaction is effected at a temperature between about 20° and 80° C.
Claim 5
Dependent Claim
26 words
A process according to claim 1, wherein about 0.9 to 1.1 mols of the acetic acid ester are employed per mol of the phosphonic acid ester.
Claim 6
Dependent Claim
27 words
A process according to claim 1, in which R 1 is C 1 -C 4 -alkyl or phenyl, or the two radicals R 1 together are 2,2-dimethyl-propane-1,3-diyl.
Claim 7
Dependent Claim
28 words
A process according to claim 1, in which R is C 1 -C 4 -alkyl, and R 2 and R 3 are both methyl or together are butane-1,4-diyl.
Claim 8
Dependent Claim
91 words
A process according to claim 1, in which R is C 1 -C 4 -alkyl, R 1 is C 1 -C 4 -alkyl or phenyl, or the two radicals R 1 together are 2,2-dimethyl-propane-1,3-diyl, R 2 and R 3 are both methyl or together are butane-1,4-diyl, and R 4 is methyl or ethyl, and wherein the reaction is effected in an inert organic solvent at a temperature between about 20° and 80° C. employing about 0.9 to 1.1 mols of the acetic acid ester per mol of the phosphonic acid ester.
References Cited (Backward Citations)
US3644487A
Cited
US4083863A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-12-18 | 1988-06-18 | 1988-12-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-18 | 1992-06-18 | 1992-12-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-18 | 1996-06-18 | 1996-12-18 | $7700.00 | Window Closed / Lapsed |