GB790842A - Substituted cyclopentenes and methods of preparing same - Google Patents

Substituted cyclopentenes and methods of preparing same

Info

Publication number
GB790842A
GB790842A GB2053956A GB2053956A GB790842A GB 790842 A GB790842 A GB 790842A GB 2053956 A GB2053956 A GB 2053956A GB 2053956 A GB2053956 A GB 2053956A GB 790842 A GB790842 A GB 790842A
Authority
GB
United Kingdom
Prior art keywords
cyclopentenyl
alkali metal
ketobutyrate
ethyl
cyclopenten
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
GB2053956A
Inventor
Howard Russell Guest
Harry Adams Stansbury Jr
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Priority to GB2053956A priority Critical patent/GB790842A/en
Publication of GB790842A publication Critical patent/GB790842A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/242—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings

Landscapes

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

Abstract

The invention comprises 2-(2-cyclopentenyl)-3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one represented by the formula: <FORM:0790842/IV (b)/1> and (a) a process for preparing ethyl 4-(2-cyclopentenyl)-3-ketobutyrate which comprises the steps of reacting cyclopentadiene with hydrogen chloride to produce 2-cyclopentenyl chloride, heating an alkali metal derivative of acetoacetic ester with the 2-cyclopentenyl chloride to produce ethyl 2-(2-cyclopentenyl)-3-ketobutyrate, subjecting the 2-(2-cyclopentenyl)3-ketobutyrate to ketonic hydrolysis in the presence of an aqueous solution of an alkyl metal hydroxide, acidifying the reaction mixture with aqueous sulphuric acid, then distilling to form 2-cyclopentenyl acetone and heating the 2-cyclopentenyl acetone with diethyl carbonate in the presence of an alkali metal alcoholate to form ethyl 4 - (2 - cyclopentenyl) - 3 - ketobutyrate; (b) a process in which the ethyl 4-(2-cyclopentenyl)-3-ketobutyrate prepared by the latter process is converted to the alkali metal salt of 4-(2 - cyclopentenyl) - 3 - ketobutyric acid by reaction with aqueous alkali metal hydroxide; (e) a process in which the alkali metal salt prepared by the latter process is reacted with an aqueous solution of pyruvic aldehyde to form 6-(2 - cyclopentenyl) - 3 - hydroxyhexane - 2,5-dione; and (d) a process in which the 6-(2-cyclopentenyl) - 3 - hydroxyhexane - 2,5 - dione prepared by the latter process is treated with a substantially 2 per cent by weight aqueous solution of alkali metal hydroxide to convert it to 2 - (2 - cyclopentenyl) - 3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one. In the example 2 - (2 - cyclopentenyl) - 3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one is obtained by a process comprising the above steps and is purified by conversion to the semicarbazone followed by hydrolysis.
GB2053956A 1954-06-22 1954-06-22 Substituted cyclopentenes and methods of preparing same Expired GB790842A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2053956A GB790842A (en) 1954-06-22 1954-06-22 Substituted cyclopentenes and methods of preparing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2053956A GB790842A (en) 1954-06-22 1954-06-22 Substituted cyclopentenes and methods of preparing same

Publications (1)

Publication Number Publication Date
GB790842A true GB790842A (en) 1958-02-19

Family

ID=10147562

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2053956A Expired GB790842A (en) 1954-06-22 1954-06-22 Substituted cyclopentenes and methods of preparing same

Country Status (1)

Country Link
GB (1) GB790842A (en)

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