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 thereof

Info

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
Application number
GB7715/49A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Distillation Products Inc
Original Assignee
Distillation Products Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Distillation Products Inc filed Critical Distillation Products Inc
Publication of GB663791A publication Critical patent/GB663791A/en
Expired legal-status Critical Current

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.
GB7715/49A 1948-03-23 1949-03-22 Improvements in and relating to the synthesis of ª‡, ª‰-unsaturated aldehydes and amine derivatives thereof Expired GB663791A (en)

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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
BE488038A (en)
FR983634A (en) 1951-06-26

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