GB1107866A - Alkylidene acetic acid derivatives - Google Patents

Alkylidene acetic acid derivatives

Info

Publication number
GB1107866A
GB1107866A GB13031/65A GB1303165A GB1107866A GB 1107866 A GB1107866 A GB 1107866A GB 13031/65 A GB13031/65 A GB 13031/65A GB 1303165 A GB1303165 A GB 1303165A GB 1107866 A GB1107866 A GB 1107866A
Authority
GB
United Kingdom
Prior art keywords
alkyl
radical
formula
alkylidene
acetic acid
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
GB13031/65A
Inventor
Hartmut Hauth
Dietrich Stauffacher
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of GB1107866A publication Critical patent/GB1107866A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/202—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a naphthalene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal 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
    • C07C45/511—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 singly bound oxygen functional groups to >C = O groups
    • C07C45/513—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 singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • 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
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds of Formula I <FORM:1107866/C2/1> <FORM:1107866/C2/2> are prepared by reacting the corresponding cyclic ketone with a (C1- 4-alkoxy) acetylene in presence of BF3 and an inert organic solvent, the alkoxyacetylene being added portionwise to the ketone and BF3 at a rate such that the temperature does not exceed 20 DEG C., the reaction being continued at a temperature from 0 DEG to the b.p. of the solution, and the product being optionally separated, where applicable, into cis- and transisomers. In the formula, R1 is H or C1- 4 alkyl, R6 is C1- 4 alkyl, each of R2, R3, R4, R5 is H, C1- 4 alkyl, R6 is C1- 4 alkyl, each of R2, R3, R4, R5 is H, C1- 4 alkyl, or (optionally substituted) cycloalkyl or aryl, or two of R2, R3, R4, R5 together are a hydrocarbon radical which with the cyclohexane ring atoms form a bicyclic monoterpenylide radical, a tetralylidene radical or a totally or partially hydrogenated phenanthrylidene radical. Compounds of Formula Ia, where R11, R12, R13 and R14 are H or Me, x - y is CH-CH2 se.
GB13031/65A 1964-04-17 1965-03-26 Alkylidene acetic acid derivatives Expired GB1107866A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH501464A CH452509A (en) 1964-04-17 1964-04-17 Process for the preparation of new α, B-unsaturated esters
CH307165 1965-03-05
CH307065 1965-03-05

Publications (1)

Publication Number Publication Date
GB1107866A true GB1107866A (en) 1968-03-27

Family

ID=27174109

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13031/65A Expired GB1107866A (en) 1964-04-17 1965-03-26 Alkylidene acetic acid derivatives

Country Status (6)

Country Link
AT (1) AT265237B (en)
BE (1) BE662646A (en)
CH (1) CH452509A (en)
ES (1) ES311822A1 (en)
GB (1) GB1107866A (en)
NL (1) NL6504614A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354681A2 (en) * 1988-07-28 1990-02-14 Ici Americas Inc. Ultraviolet radiation absorbing naphthalenylidene compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354681A2 (en) * 1988-07-28 1990-02-14 Ici Americas Inc. Ultraviolet radiation absorbing naphthalenylidene compositions
EP0354681A3 (en) * 1988-07-28 1991-04-03 Ici Americas Inc. Ultraviolet radiation absorbing naphthalenylidene compositions

Also Published As

Publication number Publication date
AT265237B (en) 1968-10-10
NL6504614A (en) 1965-10-18
CH452509A (en) 1968-03-15
BE662646A (en) 1965-10-18
ES311822A1 (en) 1965-07-01

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