GB960003A - Process for condensing an aldehyde with a compound containing at least two active hydrogen atoms on the same carbon atom - Google Patents
Process for condensing an aldehyde with a compound containing at least two active hydrogen atoms on the same carbon atomInfo
- Publication number
- GB960003A GB960003A GB29055/60A GB2905560A GB960003A GB 960003 A GB960003 A GB 960003A GB 29055/60 A GB29055/60 A GB 29055/60A GB 2905560 A GB2905560 A GB 2905560A GB 960003 A GB960003 A GB 960003A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aldehyde
- hydrogen atoms
- condensing
- active hydrogen
- acrolein
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 title abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 229910052799 carbon Inorganic materials 0.000 title abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract 2
- 159000000003 magnesium salts Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- GEKRISJWBAIIAA-UHFFFAOYSA-N 5-methylhexanal Chemical compound CC(C)CCCC=O GEKRISJWBAIIAA-UHFFFAOYSA-N 0.000 abstract 1
- LCEHKIHBHIJPCD-UHFFFAOYSA-N 6-methylheptanal Chemical compound CC(C)CCCCC=O LCEHKIHBHIJPCD-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Chemical group 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 1
- 239000002738 chelating agent Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- -1 styryl hexyl ketone Chemical compound 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An a ,b unsaturated compound is obtained by condensing an aldehyde with a compound containing at least two active hydrogen atoms on the same carbon atom in the presence of an organic magnesium salt soluble in the reaction mixture. Active hydrogen atoms are defined as hydrogen atoms attached to carbon atoms adjacent to or in conjunction with electron withdrawing groups such as aldehyde, keto, nitro, nitrile, carboxylic acid or carboxylic ester groups. The aldehyde may be aliphatic or aromatic and may contain alkoxy, amino, halogen, nitro or nitrile substituents. The magnesium salt may be derived from an organic, e.g. carboxylic acid, a phenol, a thiophenol or a chelating agent and may be used in proportions of about 0.001 to about 0.05 mole per mole of total reactants. Temperatures of about 50-400 DEG C. are mentioned. In examples, a -isoamyl-b -isohexyl acrolein is obtained from the condensation of isoheptaldehyde (acting as both reactants), a -isohexyl-b -isoheptyl acrolein from isooctaldehyde, a -n-amyl-b -n-hexyl acrolein from n-heptaldehyde, and styryl hexyl ketone by condensing benzaldehyde with 2-octanone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84220559A | 1959-09-25 | 1959-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB960003A true GB960003A (en) | 1964-06-10 |
Family
ID=25286764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29055/60A Expired GB960003A (en) | 1959-09-25 | 1960-08-23 | Process for condensing an aldehyde with a compound containing at least two active hydrogen atoms on the same carbon atom |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1138384B (en) |
| GB (1) | GB960003A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3381039A (en) * | 1963-07-18 | 1968-04-30 | Hoffmann La Roche | 1, 1-diethoxy-4-cyclohexylidene butane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545261A (en) * | 1947-10-08 | 1951-03-13 | Chemical Elaborations Inc | Catalysis of addition reactions |
| US2666771A (en) * | 1948-12-09 | 1954-01-19 | Fmc Corp | Catalyzing organic isomerization reactions with active magnesia |
-
1960
- 1960-08-23 GB GB29055/60A patent/GB960003A/en not_active Expired
- 1960-09-13 DE DEG30483A patent/DE1138384B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3381039A (en) * | 1963-07-18 | 1968-04-30 | Hoffmann La Roche | 1, 1-diethoxy-4-cyclohexylidene butane |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1138384B (en) | 1962-10-25 |
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