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US3979471A
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Process for synthesizing ethylenic compounds
Assignee: Bpifrance Financement SA
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Filing: 1974-08-02
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Granted: 1976-09-07
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Expires: 1994-08-02
Abstract
Abstract The invention relates to a process for the preparation of ethylenic compounds and to certain novel ethylenic compounds produced by the process. The process comprises the reaction of an appropriate carbonyl compound with a sulphone to obtain an alcohol sulphone which is then reduced to obtain the desired ethylenic compound.
Inventors
- 👤 Marc Julia
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:36
CPC Classifications
C; C07; C07C; C07C317/00; C07C1/00; C07C1/32; C07C1/321; C07C1/322; Y; Y02; Y02P; Y02P30/00; Y02P30/20; Y02P30/40; Y10; Y10S; Y10S585/00; Y10S585/929; Y10S585/93; Y10S585/934
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
169 words
A process for preparing ethylenic compounds with the formula: ##EQU1## wherein: R 1 and R 3 are selected from the group consisting of hydrogen and CH 3 ; R 2 is selected from the group consisting of hydrogen, aromatic hydrocarbon radical, and a saturated or unsaturated, linear or branched aliphatic hydrocarbon; R 4 is selected from the group consisting of phenyl and a saturated or unsaturated linear or branched aliphatic hydrocarbon, where R 3 and R 4 may be joined to form a ring structure; which comprises the steps of reacting in the presence of a basic agent selected from the oxides, hydroxides, amides, hydrides and alcoholates of an alkali metal ##EQU2## wherein R 3 and R 4 are as set forth above and ##EQU3## wherein R 1 and R 2 are as set forth above and R is selected from the group consisting of alkyl, aryl and cycloalkyl to form an alcohol sulphone of the formula: ##EQU4## which sulphone is treated with an alkali metal amalgam reducing agent.
Claim 2
Dependent Claim
169 words
A process for preparing ethylenic compounds with the formula: ##EQU1## wherein: R 1 and R 3 are selected from the group consisting of hydrogen and CH 3 ; R 2 is selected from the group consisting of hydrogen, aromatic hydrocarbon radical, and a saturated or unsaturated, linear or branched aliphatic hydrocarbon; R 4 is selected from the group consisting of phenyl and a saturated or unsaturated linear or branched aliphatic hydrocarbon, where R 3 and R 4 may be joined to form a ring structure; which comprises the steps of reacting in the presence of a basic agent selected from the oxides, hydroxides, amides, hydrides and alcoholates of an alkali metal ##EQU2## wherein R 3 and R 4 are as set forth above and ##EQU3## wherein R 1 and R 2 are as set forth above and R is selected from the group consisting of alkyl, aryl and cycloalkyl to form an alcohol sulphone of the formula: ##EQU4## which sulphone is treated with an alkali metal amalgam reducing agent.
Claim 3
Dependent Claim
33 words
The process of claim 1 wherein formula A is selected from the group consisting of acetone, methylethylacetone, methylvinylacetone, 6-methyl-2-heptenone, cyclohexanone, acetophenone, acetaldehyde, propionic aldehyde, valeric aldehyde, benzaldehyde, acrolein, methacrolein, crotonaldehyde, senecioic aldehyde, citral.
Claim 4
Dependent Claim
24 words
The process of claim 1 wherein the step of reacting A and B ia carried out at a temperature range between ambiant and -80°C.
Claim 5
Dependent Claim
34 words
The process of claim 1 wherein the step of reacting A and B is carried out using the basic agent in a ratio of 1 to 1.2 mols per mol of the sulphone (B).
Claim 6
Dependent Claim
31 words
The process of claim 1 wherein the first step is carried out in an inert solvent selected from the group consisting of aliphatic hydrocarbon, aromatic hydrocarbons, alcohols, ethers and polar solvents.
Claim 7
Dependent Claim
22 words
The process of claim 1, wherein the second step (treating alcohol sulphone) is carried out at a temperature between ambiant and -50°C.
Claim 8
Dependent Claim
31 words
The process of claim 1, wherein the second step is carried out with a molar quantity of alkali metal amalgam equal to or greater than that of the alcohol sulphone (C).
Claim 9
Dependent Claim
32 words
The process of claim 1, wherein the second step is carried out in an inert solvent selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, alcohols and linear and cyclic ether.
Claim 10
Dependent Claim
28 words
In the (The) process of claim 1, the step wherein the sulphone alcohol (C) is esterified before being subjected to treatment with an alkali metal amalgam reducing agent.
Claim 11
Dependent Claim
34 words
The process of claim 9, wherein the sulphone alcohol is esterified by a compound selected from the group consisting of organo sulphonic acids, chloride and anhydride thereof, and carboxylic acids, chloride and anhydride thereof.
Claim 12
Dependent Claim
28 words
The process of claim 10, wherein the compound used for esterification is selected from the group consisting of methylsulphonic acid chloride and acetic anhydride p-toluene sulphonic acid chloride.
References Cited (Backward Citations)
US3830862A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |