GB663791A - Improvements in and relating to the synthesis of ª‡, ª‰-unsaturated aldehydes and amine derivatives thereof - Google Patents
Improvements in and relating to the synthesis of ª‡, ª‰-unsaturated aldehydes and amine derivatives thereofInfo
- Publication number
- GB663791A GB663791A GB7715/49A GB771549A GB663791A GB 663791 A GB663791 A GB 663791A GB 7715/49 A GB7715/49 A GB 7715/49A GB 771549 A GB771549 A GB 771549A GB 663791 A GB663791 A GB 663791A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ketone
- ionylidene
- aniline
- reacted
- amine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/18—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by nitrogen atoms
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An a ,b -unsaturated aldehyde is prepared by reacting together an a ,b -unsaturated alcohol, a primary aromatic amine, and a ketone in the presence of either an aluminium alkoxide or a p magnesium alkoxide in order to produce a Schiffs base, and thereafter hydrolysing the Schiffs base to the a ,b -unsaturated aldehyde. Before hydrolysis the Schiffs base may be isolated. Specified are: alcohols: b -ionylidene ethanol, Vitamin A, and cinnamyl alcohol; ketones: diethyl-, dibutyl-, and methyl ethyl ketone, benzophenone, acetophenone, cyclohexanone, and fluorenone; amines: aniline, a - or b -naphthylamine, o-, m- or p-toluidine, and xylidines. In examples: (1) b -ionylidene ethanol is refluxed with aniline, diethyl ketone and aluminium ter-butoxide. The product is reacted with dilute HCl to give b -ionylidene acetaldehyde. In a similar manner, (11) Vitamin A and (12) cinnamyl alcohol are reacted to give the corresponding anils which are hydrolysed with hydrochloric acid to the aldehydes. The b -ionylidene acetaldehyde obtained in (1) may be reacted with acetone in the presence of aluminium isopropoxide to yield the "C18 ketone". Other examples, some for comparison purposes, show the use as amine in place of the aniline in (1) of (3) naphthylamine, (4) 4-amino-1,3-dimethyl-benzene, (5) o-toluidine, (6) diphenylamine, (7) n-butylamine, (8) cyclohexylamine, (99) ethylene diamine, and (10) pyridine, and in (2) no amine is employed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US663791XA | 1948-03-23 | 1948-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB663791A true GB663791A (en) | 1951-12-27 |
Family
ID=22069126
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7715/49A Expired GB663791A (en) | 1948-03-23 | 1949-03-22 | Improvements in and relating to the synthesis of ª‡, ª‰-unsaturated aldehydes and amine derivatives thereof |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE488038A (en) |
FR (1) | FR983634A (en) |
GB (1) | GB663791A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2846431A (en) * | 1951-10-01 | 1958-08-05 | Permanente Cement Company | Water soluble thermo-setting resin and method for its manufacture |
-
0
- BE BE488038D patent/BE488038A/xx unknown
-
1949
- 1949-03-22 GB GB7715/49A patent/GB663791A/en not_active Expired
- 1949-03-23 FR FR983634D patent/FR983634A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE488038A (en) | |
FR983634A (en) | 1951-06-26 |
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