GB665146A - Improvements in or relating to the preparation of a new unsaturated ketone - Google Patents

Improvements in or relating to the preparation of a new unsaturated ketone

Info

Publication number
GB665146A
GB665146A GB775849D GB775849D GB665146A GB 665146 A GB665146 A GB 665146A GB 775849 D GB775849 D GB 775849D GB 775849 D GB775849 D GB 775849D GB 665146 A GB665146 A GB 665146A
Authority
GB
United Kingdom
Prior art keywords
methylpenta
prepared
dien
acetone
methylocta
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
GB775849D
Inventor
Sir Ian Morris Heilbron
Basil Charles Leicester Weedon
Ewart Ray Herbert Jones
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 GB775849D priority Critical patent/GB665146A/en
Publication of GB665146A publication Critical patent/GB665146A/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
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • 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
    • C07C45/70—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 with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 with functional groups containing oxygen only in singly bound form being hydroxy groups

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 6-methylocta, 3 : 5 : 7-trien-2-one represented by the structural formula <FORM:0665146/IV (b)/1> an unsaturated ketone of formula C9H13O, having the refracture index ( <FORM:0665146/IV (b)/2> ) 1.6025, light absorption max. 304 mm , E1 per cent1 cm. 2,400 and e 32,600. This compound is prepared by reacting 3-methylpenta-2-4-dien-1-ol with acetone in the presence of aluminium tertiary butoxide. Preferably an excess of acetone or an organic solvent inert under the reaction conditions is present as diluent, e.g. benzene, petroleum ether, dipropyl ether, dibutyl ether or mixtures of two or more of these solvents, and the process is carried out in an inert atmosphere. In an example 6-methylocta-3 : 5 : 7-trien-2-one is prepared by refluxing a solution containing 3-methylpenta-2 : 4-dien-1-ol, aluminium tert-butoxide, acetone and benzene under nitrogen, pouring the product into dilute sulphuric acid and separating and fractionating the organic layer. The starting material is prepared by shaking with dilute sulphuric acid and a trace of hydroquinone under nitrogen 3-methylpenta-1 : 4-dien-3-ol which is prepared in turn by hydrogenating 3-methylpenta-4-en-1-yn-3-ol in methanol using a palladium-charcoal catalyst.
GB775849D 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated ketone Expired GB665146A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB775849D GB665146A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated ketone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB775849D GB665146A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated ketone

Publications (1)

Publication Number Publication Date
GB665146A true GB665146A (en) 1952-01-16

Family

ID=9839155

Family Applications (1)

Application Number Title Priority Date Filing Date
GB775849D Expired GB665146A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated ketone

Country Status (1)

Country Link
GB (1) GB665146A (en)

Similar Documents

Publication Publication Date Title
US2579658A (en) 3-methyl-1-(1&#39;-hydroxy-2&#39;, 6&#39;, 6&#39;-trimethylcyclohexyl)-octa-3, 5-dien-1-yn-7-one andprocess of preparing same
GB665146A (en) Improvements in or relating to the preparation of a new unsaturated ketone
Yasuda et al. Stereoselective 1, 4-addition of dialkylaluminum benzenethiolate to vinyl oxiranes
Mukaiyama et al. Addition reaction of thiol to olefin by the use of TiCl4
Aida et al. Reaction of dibenzothiophene sulfone with alkoxides
US3009962A (en) Organic peroxides
DE1804878C3 (en) Process for the preparation of 5-isopropylidene-2-norbornene by isomerizing 5-isopropenyl-2-norbornene
DE68913236T2 (en) Process for the production of halogenated sulfones.
Toda et al. Intramolecular Cyclization of o, o′-Dihydroxydiphenyldiacetylene
US2606930A (en) 6-methylocta-3:5:7-trien-2-one
IE42827B1 (en) Preparation of 3-phenoxybenzaldehydes
US3646222A (en) Method for production of substituted hydroquinones
ES483367A1 (en) Process for the preparation of glycidyl esters of aromatic polycarboxylic acids.
Capozzi et al. Stable sulfinic acids from the ene reaction of methyl-substituted allenes with sulfur dioxide
Javaid et al. Acid-Catalyzed Oxidation of Olefins with Selenium Dioxide
EP0620217B1 (en) Process for the preparation of 4-methyl-pyrimidines
Robinson et al. Direct formation of cyclic sulfates utilising hypervalent iodine species and sulfur trioxide adducts
US2614124A (en) Preparation of new unsaturated
Satoh et al. Bis (diisobutylaluminum) 1, 2-ethanedithiolate: A reagent in the conversion of oxyacetals to thioacetals.
US2944066A (en) Process for the production of
GB1101255A (en) Ketones
GB742949A (en) Improvements in and relating to the condensation of di-alkyl succinates
US3067235A (en) Oxidation of alkyl boron compounds
US4251666A (en) Method of producing thiophene
GB935610A (en) 3ªá-amino-pregnane compounds