GB627453A - Improvements in and relating to the preparation of derivatives of cyclohexene - Google Patents

Improvements in and relating to the preparation of derivatives of cyclohexene

Info

Publication number
GB627453A
GB627453A GB18977/47A GB1897747A GB627453A GB 627453 A GB627453 A GB 627453A GB 18977/47 A GB18977/47 A GB 18977/47A GB 1897747 A GB1897747 A GB 1897747A GB 627453 A GB627453 A GB 627453A
Authority
GB
United Kingdom
Prior art keywords
methyl
substituted
ethynylcyclohexene
trimethyl
dimethyl
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
GB18977/47A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB18977/47A priority Critical patent/GB627453A/en
Publication of GB627453A publication Critical patent/GB627453A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • 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

Cyclohexene derivatives of general formula RC­CH, wherein R is a cyclohex-1-enyl group which is substituted by one, two or three methyl groups in the 2 and/or 6 positions, are prepared by passing the corresponding 1-ethynyl cyclohexanol in the vapour phase over a heated metal phosphate catalyst, that of aluminium being preferred. The reaction may be effected at reduced pressures or in the presence of an inert gas such as nitrogen, and temperatures of 250-300 DEG C., especially 270 DEG C., are preferred. In examples: (1) 2-methyl-, (2) 2 : 2-dimethyl-and (3) 2 : 6 : 6-trimethyl-1-ethynylcyclohexanol are passed over porcelain coated with aluminium phosphate to give 2-methyl-, 2 : 2-dimethyl-, and 2 : 6 : 6-trimethyl-1-ethynylcyclohexene respectively. The substituted cyclohexanols used as starting materials are obtained by treating in liquid ammonia solution an alkali metal derivative of acetylene with the correspondingly substituted cyclohexanone. In the Provisional Specification it is stated that R of the above formula may be unsubstituted or contain one, two or three lower alkyl substituents and an example (2) is given of the preparation of 1-ethynylcyclohexene.
GB18977/47A 1947-07-16 1947-07-16 Improvements in and relating to the preparation of derivatives of cyclohexene Expired GB627453A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB18977/47A GB627453A (en) 1947-07-16 1947-07-16 Improvements in and relating to the preparation of derivatives of cyclohexene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB18977/47A GB627453A (en) 1947-07-16 1947-07-16 Improvements in and relating to the preparation of derivatives of cyclohexene

Publications (1)

Publication Number Publication Date
GB627453A true GB627453A (en) 1949-08-09

Family

ID=10121687

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18977/47A Expired GB627453A (en) 1947-07-16 1947-07-16 Improvements in and relating to the preparation of derivatives of cyclohexene

Country Status (1)

Country Link
GB (1) GB627453A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622102A (en) * 1952-12-16 Unsaturated carbinol and process
US2622104A (en) * 1952-12-16 Unsaturated carbinol and process of
US2672481A (en) * 1950-11-25 1954-03-16 Eastman Kodak Co Polyene intermediates and methods of making same
US2993864A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Ethynylcyclohexyl compounds as corrosion inhibitors
US2993863A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Halogenated propargyl alcohols as corrosion inhibitors
US2993862A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Acetylenic glycols as corrosion inhibitors
US2993865A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Corrosion inhibitors for aluminum
US4284654A (en) 1979-10-26 1981-08-18 International Flavors & Fragrances Inc. Use of 1-hydroxy-1-ethynyl-2,2,6-trimethyl cyclohexane in augmenting or enhancing the aroma or taste of foodstuffs
CN101481344B (en) * 2008-01-10 2012-06-13 浙江新和成股份有限公司 Preparation of tetradecanal
WO2019079365A1 (en) * 2017-10-19 2019-04-25 Dow Silicones Corporation Polyorganosiloxane compositions containing a 2-substituted-1-alkynyl-1-cyclohexanol useful as a hydrosilylation reaction inhibitor

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622102A (en) * 1952-12-16 Unsaturated carbinol and process
US2622104A (en) * 1952-12-16 Unsaturated carbinol and process of
US2672481A (en) * 1950-11-25 1954-03-16 Eastman Kodak Co Polyene intermediates and methods of making same
US2993864A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Ethynylcyclohexyl compounds as corrosion inhibitors
US2993863A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Halogenated propargyl alcohols as corrosion inhibitors
US2993862A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Acetylenic glycols as corrosion inhibitors
US2993865A (en) * 1956-08-02 1961-07-25 Dow Chemical Co Corrosion inhibitors for aluminum
US4284654A (en) 1979-10-26 1981-08-18 International Flavors & Fragrances Inc. Use of 1-hydroxy-1-ethynyl-2,2,6-trimethyl cyclohexane in augmenting or enhancing the aroma or taste of foodstuffs
CN101481344B (en) * 2008-01-10 2012-06-13 浙江新和成股份有限公司 Preparation of tetradecanal
WO2019079365A1 (en) * 2017-10-19 2019-04-25 Dow Silicones Corporation Polyorganosiloxane compositions containing a 2-substituted-1-alkynyl-1-cyclohexanol useful as a hydrosilylation reaction inhibitor
CN111032604A (en) * 2017-10-19 2020-04-17 美国陶氏有机硅公司 Polyorganosiloxane compositions containing 2-substituted-1-alkynyl-1-cyclohexanols useful as hydrosilylation reaction inhibitors
CN111032604B (en) * 2017-10-19 2020-10-30 美国陶氏有机硅公司 Polyorganosiloxane compositions containing 2-substituted-1-alkynyl-1-cyclohexanols useful as hydrosilylation reaction inhibitors
US10876019B2 (en) 2017-10-19 2020-12-29 Dow Silicones Corporation Polyorganosiloxane compositions containing a 2-substituted-1-alkynyl-1-cyclohexanol useful as a hydrosilylation reaction inhibitor

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