GB1007828A - Cyclohexadiene derivatives - Google Patents

Cyclohexadiene derivatives

Info

Publication number
GB1007828A
GB1007828A GB2381562A GB2381562A GB1007828A GB 1007828 A GB1007828 A GB 1007828A GB 2381562 A GB2381562 A GB 2381562A GB 2381562 A GB2381562 A GB 2381562A GB 1007828 A GB1007828 A GB 1007828A
Authority
GB
United Kingdom
Prior art keywords
chloro
chlorobutadiene
reacting
produced
cyclohexadiene
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
GB2381562A
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Publication of GB1007828A publication Critical patent/GB1007828A/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
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/798—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/42—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/543—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a six-membered ring

Landscapes

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

Abstract

Conjugated cyclohexadienes of the formula <FORM:1007828/C4-C5/1> in which at least one of X and Y is aryl or C8-C12 aralkyl or alkaryl are obtained by dehydrohalogenation of a 3-halo-4-cyclohexene having an aryl, aralkyl or alkaryl radical in the 1- and/or 2-position, by treatment with an alkali. In an example 1-phenyl-1, 3-cyclohexadiene is prepared by heating with potassium hydroxide 3-bromo-2-phenylcyclohexene-4.ALSO:Conjugated cyclohexadienes of a general formula <FORM:1007828/C2/1> wherein X and Y are the same or different and are hydrogen atoms, -COOH radicals, -COOR radicals wherein R is an alkyl or an aryl group, -CN, -CHO, radicals -RCO wherein R is an alkyl or an aryl group, haloalkyl radicals having from 1 to 8 carbon atoms, or aryl, or aralkyl or alkaryl radicals having from 8 to 12 carbon atoms, are produced by dehydrohalogenating by treatment with an alkaline substance, e.g. potassium hydroxide a 3-halo-4-cyclohexene, e.g. 3-chloro-4-cyclohexene substituted in at least one of the positions 1 and 2 of the hexene nucleus by carboxylic, carboxylic anhydride, carboxylic ester, cyano, keto, aldehyde, dioxolan, haloalkyl, aryl, alkaryl or aralkyl groups. The 2,4-cyclohexadiene-1,2-dicarboxylic acids produced may be converted to the corresponding anhydride, e.g. by refluxing acetic anhydride or to the half ester or di-ester. In example, 2,4 - cyclohexadiene - 1 - 2 - dicarboxylic acid is prepared by treating with alcoholic potassium hydroxide 3 - chloro - 4 - cyclohexene - 1,3 - dicarboxylic anhydride obtained by reacting trans - 1 - chloro - butadiene with maleic anhydride. In another example the Diels-Alder adduct of 1-chlorobutadiene and dibutyl maleate was treated with alcoholic potassium hydroxide to produce dibutyl - 2,4 - cyclohexadiene - 1,2-dicarboxylate. In other examples, 1,3-cyclohexadiene-1-nitrile is obtained from 2 chloro-3-cyclohexene (produced by reacting 1 chlorobutadiene and acrylonitrile); 1,3-cyclohexadienyl methyl ketone from 2-chloro-3-cyclohexene (produced by reacting 1-chlorobutadiene and acrylonitrile); 1,3-cyclohexadienyl methyl ketone from 2-chloro-3-cyclohexene (produced by reacting 1-chlorobutadiene and acrylonitrile; 1,3-cyclohexadienyl methyl ketone from 2-chloro-3-cyclo-hexenyl-1 methyl ketone (produced by reacting 1-chlorobutadiene with methyl vinyl ketone). In the above examples, 1-bromo or 1-iodo may be used instead of 1-chlorobutadiene-1,3. In other examples, 1,3-cyclohexadiene - 1 - carboxaldehyde is obtained from 2 - (2 - chloro - 3 - cyclohexenyl)-dioxolan obtained by reacting p-toluene sulphonic acid with 2-chlorocylohex-3-ene-1-carboxaldehyde (produced by reacting 1 chlorobutadiene with acrolein); 2-benzoyl 2,4-cyclohexadiene from phenyl 2-chloro-3 cyclo hexenyl ketone (produced by reacting 1-chlorobutadiene with acrylophenone); 1-trifluoromethyl-2-4-cyclohexadiene from 1-trifluoromethyl-2 chloro 3-cyclohexene (produced by reacting 1-chlorobutadiene and 1,1,1-trifluoropropene); 6-(4-methylphenyl) - 2,4 - cyclohexadiene - 1 - carboxylic acid from 2-chloro-6-(4-methyl-phenyl)-3-cyclohexene carboxylic acid (produced by reacting 1 - chlorobutadiene and 4 - methyl cinnanic acid).
GB2381562A 1961-06-21 1962-06-20 Cyclohexadiene derivatives Expired GB1007828A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11851661A 1961-06-21 1961-06-21

Publications (1)

Publication Number Publication Date
GB1007828A true GB1007828A (en) 1965-10-22

Family

ID=22379090

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2381562A Expired GB1007828A (en) 1961-06-21 1962-06-20 Cyclohexadiene derivatives

Country Status (1)

Country Link
GB (1) GB1007828A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288847A (en) * 1964-04-13 1966-11-29 Monsanto Co Preparation of 1, 4-cyclohexadiene-1-carboxylic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288847A (en) * 1964-04-13 1966-11-29 Monsanto Co Preparation of 1, 4-cyclohexadiene-1-carboxylic acid

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