GB650289A - Process for the isomerisation of keto-octahydrophenanthrene carboxylic acid esters - Google Patents

Process for the isomerisation of keto-octahydrophenanthrene carboxylic acid esters

Info

Publication number
GB650289A
GB650289A GB17773/48A GB1777348A GB650289A GB 650289 A GB650289 A GB 650289A GB 17773/48 A GB17773/48 A GB 17773/48A GB 1777348 A GB1777348 A GB 1777348A GB 650289 A GB650289 A GB 650289A
Authority
GB
United Kingdom
Prior art keywords
octahydrophenanthrene
keto
carboxylic acid
alkaline
group
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
GB17773/48A
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.)
C I B A Ltd
Original Assignee
C I B A 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 C I B A Ltd filed Critical C I B A Ltd
Publication of GB650289A publication Critical patent/GB650289A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group 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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

1 - Keto - 2 - methyl - 7 - alkoxy - 1 : 2 : 3 : 4 : 9 : 10 : 11 : 12 - octahydrophenanthrene - 2 - carboxylic acid methyl esters are converted into stereoisomeric forms by treatment with an alkaline agent; the starting material is the 7-methoxy compound which melts at 87-89 DEG C. or a homologue which has the same steric p configuration (e.g. the ethoxy compound), and may be obtained by separation of a mixture of the isomers described in Specification 645,765. The alkaline agent may be an alkali or alkaline earth hydroxide, carbonate or bicarbonate, ammonia, a strong organic base such as trimethylbenzyl-ammonium hydroxide or an alkaline adsorptive agent such as alumina. The process may be carried out in the presence of an organic solvent and in the presence or absence of water. Examples show the production of 1 - keto - 2 - methyl - 7 - methoxy - 1 : 2 : 3 : 4 : 9 : 10 : 11 : 12 - octahydrophenanthrene - 2 - carboxylic acid methyl ester melting at 133-135 DEG C. In the Specification as open to inspection under Sect. 91, the process is applied to 1-keto-2 - alkyl - 1 : 2 : 3 : 4 : 9 : 10 : 11 : 12 - octahydrophenanthrene - 2 - carboxylic acid esters in general. The 2-alkyl group may be ethyl, and the ethyl, propyl and butyl esters are mentioned. The 7-position may be unsubstituted, or may contain a free hydroxy group, an aralkoxy group such as benzyloxy or an acyloxy group, e.g. acetoxy, propionoxy or benzoyloxy. This subject-matter does not appear in the Specification as accepted.
GB17773/48A 1947-07-10 1948-07-01 Process for the isomerisation of keto-octahydrophenanthrene carboxylic acid esters Expired GB650289A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH650289X 1947-07-10

Publications (1)

Publication Number Publication Date
GB650289A true GB650289A (en) 1951-02-21

Family

ID=4526058

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17773/48A Expired GB650289A (en) 1947-07-10 1948-07-01 Process for the isomerisation of keto-octahydrophenanthrene carboxylic acid esters

Country Status (1)

Country Link
GB (1) GB650289A (en)

Similar Documents

Publication Publication Date Title
DE3063603D1 (en) Process for the separation of ursodeoxycholic acid from chenodeoxycholic acid and products obtained during the process
GB650289A (en) Process for the isomerisation of keto-octahydrophenanthrene carboxylic acid esters
GB1021475A (en) A process of preparing trialkali metal nitrilotriacetates
GB895145A (en) Separation of sterols
GB1001826A (en) Improvements in or relating to a tetrahydropyran derivative
GB589800A (en) Improvements relating to the separation of calcium carbonate by froth flotation
GB610723A (en) Process for the separation and purification of stereoisomeric hydrophenanthrene carboxylic acids
GB625602A (en) New calciferol esters and their process of preparation
GB646227A (en) Process for isolation of cholesterol from wool wax alcohols
GB824574A (en) Process for the fractionation of fatty acid mixtures
CA466610A (en) Process of utilizing waste liquors
GB642370A (en) Improvements in or relating to process of preparing pure crystalline salts of penicillin, and the improved pure crystalline salts of penicillin resulting therefrom
CH282380A (en) Process for the preparation of a dichloroacetimidoether.
GB632801A (en) Process for the production of a derivative of benzotetronic acid
CA445882A (en) Process for producing potassium hydroxide of high purity
AU146815B2 (en) Improvements in or relating tothe separation of fatty acids or their glycerides from derivatives containing them
GB722186A (en) Improvements relating to the production of sapogenins
JPS51118754A (en) Process for preparation of anthraquinone
GB599626A (en) Improvements in or relating to the manufacture of purified penicillin
GB913353A (en) Steroids
GB670702A (en) Improvements in or relating to the preparation of mercapto-carboxylic acids and salts and amides thereof
GB644399A (en) Improvements in or relating to the production of tertiary rosin alcohols
CA453118A (en) Process for producing unsaturated aliphatic compounds
AU2356548A (en) Improvements in or relating tothe separation of fatty acids or their glycerides from derivatives containing them
AU154243B2 (en) Improvements in process for recovering acetic acid and methanol from mixture of methyl acetate, acetic acid, methanol and water