Patent US3701048A successfully refreshed from Google Patents.
Patent US4096170A successfully refreshed from Google Patents.
US4096170A
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Preparation of esters
Assignee: Shell USA Inc
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Filing: 1977-05-12
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Granted: 1978-06-20
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Expires: 1997-05-12
Abstract
Abstract Certain cyclopropanecarboxylic acid esters also containing a cyano group are prepared by reacting an aldehyde, a salt of hydrocyanic acid and a 2-halocyclobutanone in an aprotic solvent.
Inventors
- 👤 Marinus J. van den Brink
- 👤 Roger A. Sheldon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:47
CPC Classifications
A; A01; A01N; A01N53/00; C; C07; C07C; C07C255/00; C07C255/49; C07C255/53
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
148 words
A process for the preparation of an ester of formula I ##STR3## wherein R 1 , R 2 , R 3 , and R 4 each represents an alkyl group containing from 1 to 6 carbon atoms, a cycloalkyl group containing from 3 to 6 carbon atoms, a phenyl group, an ethylenically unsaturated group containing from 2 to 4 carbon atoms, or a hydrogen atom, and R 5 represents a phenoxyphenyl group which comprises contacting (a) an aldehyde of formula II r.sup.5 --c(0)h (ii) wherein R 5 has the same meaning as in formula I, (b) an alkali metal, alkaline earth metal or tetrahydrocarbylammonium salt of hydrocyanic acid, (c) a 2-halocyclobutanone of formula III ##STR4## wherein R 1 , R 2 , R 3 and R 4 have the same meaning as in formula I and Hal represents a halogen atom, and (d) one or more aprotic solvents.
Claim 2
Dependent Claim
148 words
A process for the preparation of an ester of formula I ##STR3## wherein R 1 , R 2 , R 3 , and R 4 each represents an alkyl group containing from 1 to 6 carbon atoms, a cycloalkyl group containing from 3 to 6 carbon atoms, a phenyl group, an ethylenically unsaturated group containing from 2 to 4 carbon atoms, or a hydrogen atom, and R 5 represents a phenoxyphenyl group which comprises contacting (a) an aldehyde of formula II r.sup.5 --c(0)h (ii) wherein R 5 has the same meaning as in formula I, (b) an alkali metal, alkaline earth metal or tetrahydrocarbylammonium salt of hydrocyanic acid, (c) a 2-halocyclobutanone of formula III ##STR4## wherein R 1 , R 2 , R 3 and R 4 have the same meaning as in formula I and Hal represents a halogen atom, and (d) one or more aprotic solvents.
Claim 3
Dependent Claim
21 words
A process according to claim 1, in which the aprotic solvent is substantially immiscible with water, which is present as well.
Claim 4
Dependent Claim
21 words
A process according to claim 2, in which the substantially water-immiscible aprotic solvent comprises an alkane or a mixture of alkanes.
Claim 5
Dependent Claim
12 words
A process according to claim 3, in which the alkane is n-heptane.
Claim 6
Dependent Claim
53 words
A process according to claim 2, in which the amount of water is less than the amount required to obtain a 25%w aqueous solution with the starting amount of a water-soluble salt of hydrocyanic acid, but sufficiently large to dissolve all of this cyanide at the temperature at which the process is conducted.
Claim 7
Dependent Claim
21 words
A process according to claim 1, which is conducted at a temperature in the range of from 50° to 80° C.
Claim 8
Dependent Claim
24 words
A process according to claim 1, in which the aldehyde of formula II and the 2-halocyclobutanone of formula III are used in equimolar amounts.
Claim 9
Dependent Claim
31 words
A process according to claim 1, in which the molar ratio of the salt of hydrocyanic acid to aldehyde of formula II is in the range of from 1.0 to 1.5.
Claim 10
Dependent Claim
17 words
A process according to claim 1, in which the salt of hydrocyanic acid is an alkali-metal cyanide.
Claim 11
Dependent Claim
14 words
A process according to claim 9, in which the alkali-metal cyanide is potassium cyanide.
Claim 12
Dependent Claim
33 words
A process according to claim 1, in which R 1 , R 2 , R 3 and R 4 in formula III each represents an alkyl group having one to six carbon atoms.
Claim 13
Dependent Claim
24 words
A process according to claim 11, in which R 1 , R 2 , R 3 and R 4 each represents a methyl group.
Claim 14
Dependent Claim
18 words
A process according to claim 1, in which Hal in formula III represents a chlorine or bromine atom.
References Cited (Backward Citations)
US3835176A
Cited
US4000180A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |