GB650983A - Manufacture of octahydrophenanthrene-2-carboxylic acids and esters thereof - Google Patents

Manufacture of octahydrophenanthrene-2-carboxylic acids and esters thereof

Info

Publication number
GB650983A
GB650983A GB10371/48A GB1037148A GB650983A GB 650983 A GB650983 A GB 650983A GB 10371/48 A GB10371/48 A GB 10371/48A GB 1037148 A GB1037148 A GB 1037148A GB 650983 A GB650983 A GB 650983A
Authority
GB
United Kingdom
Prior art keywords
octahydrophenanthrene
carboxyl group
free
hydroxy group
organo
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
GB10371/48A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB650983A publication Critical patent/GB650983A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Sterically homogeneous octahydrophenanthrene-2-carboxylic acids and esters are manufactured by reacting a sterically homogeneous 1-keto-octahydrophenanthrene, containing in the 2-position a hydrocarbon radical and an esterified carboxyl group and in the 7-position a phenolic hydroxy group or a substituent convertible thereto, with an organo-metallic compound in order to introduce a hydrocarbon radical into the 1-position, directly or indirectly eliminating the resulting tertiary hydroxy group, separating the two isomers so obtained by fractional crystallization, chromatography or sublimation, and, if desired, converting the esterified carboxyl group in the 2-position into a free carboxyl group, or the substituent in the 7-position into a free hydroxy group, or both, in either order, and hydrogenating non-aromatic carbon-to-carbon multiple bonds at any desired stage after reaction with the organo-metallic compound. The starting material may be an individual racemate (obtainable by fractional crystallization, chromatography or sublimation) or an individual optically active antipode, the initial reaction product being (on account of the introduction of an additional asymmetrical carbon atom) respectively a mixture of two racemates or of two optically active antipodes, the relative proportions of which may be influenced by the reaction conditions. The other steps in the process may be carried out as described in Specification 591,994, and the various substituents present in the starting materials may be as therein enumerated. Free carboxylic and hydroxy groups in the products may be subjected to further transformations as described in the said Specification and in Specifications 622,892 and 629,118. Examples illustrate various features of the invention, using various isomers of 7-methoxy-1-keto-2-methyl-1 : 2 : 3 : 4 : 9 : 10 : 11 : 12-octahydrophenanthrene-2-carboxylic acid methyl ester as starting materials, and further conversions of certain of the products of the examples are described in detail.
GB10371/48A 1947-04-24 1948-04-14 Manufacture of octahydrophenanthrene-2-carboxylic acids and esters thereof Expired GB650983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH650983X 1947-04-24

Publications (1)

Publication Number Publication Date
GB650983A true GB650983A (en) 1951-03-07

Family

ID=4526107

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10371/48A Expired GB650983A (en) 1947-04-24 1948-04-14 Manufacture of octahydrophenanthrene-2-carboxylic acids and esters thereof

Country Status (1)

Country Link
GB (1) GB650983A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE936269C (en) * 1952-08-26 1955-12-07 Ciba Geigy Process for the preparation of new octahydrophenanthrene-2-carboxylic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE936269C (en) * 1952-08-26 1955-12-07 Ciba Geigy Process for the preparation of new octahydrophenanthrene-2-carboxylic acids

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