GB702012A - Process for the preparation of intermediates in the synthesis of steroids and the products of such process - Google Patents

Process for the preparation of intermediates in the synthesis of steroids and the products of such process

Info

Publication number
GB702012A
GB702012A GB24536/51A GB2453651A GB702012A GB 702012 A GB702012 A GB 702012A GB 24536/51 A GB24536/51 A GB 24536/51A GB 2453651 A GB2453651 A GB 2453651A GB 702012 A GB702012 A GB 702012A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methoxy
methyl
tetralone
acid
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
GB24536/51A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB702012A publication Critical patent/GB702012A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

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 1-hydroxy-4-methoxy-7-keto-13-methyl-5 : 6 : 7 : 9 : 10 : 13-hexahydrophenanthrene <FORM:0702012/IV(b)/1> which is prepared by reacting 5-hydroxy-8-methoxy-1-methyl-tetralone-2 with diethylamino-butanone-2 in an anhydrous organic solvent in the presence of an alkaline condensing agent. Specified condensing agents include alkali metal alkoxides and amides, in particular potassium ethoxide. The intermediate 5-hydroxy-8-methoxy-1-methyl-tetralone-2 is prepared as follows:-Hydroquinone dimethyl ether is reacted with succinic anhydride in presence of aluminium chloride to give b -[2-hydroxy - 5 - methoxybenzoyl] - propionic acid, which is hydrogenated to g -[2-hydroxy-5-methoxy phenyl]-butyric acid. This upon ringclosure yields 5-hydroxy-8-methoxy tetralone-1, which on treatment with methyl magnesium iodide, followed by vacuum distillation gives 1 - hydroxy - 4 - methoxy - 5 - methyl - 7 : 8 - dihydro-naphthalene. This substance is reacted with osmium tetroxide to produce 1 : 5 : 6-trihydroxy - 4 - methoxy - 5 - methyl - 5 : 6 : 7 : 8 - tetrahydro-naphthalene, which on treatment with acid yields the desired 5-hydroxy-8-methoxy - 1 - methyl - tetralone - 2. In an example, diethylamino-butanone-2 is converted to its methiodide, which is then treated with anhydrous ethanolic 5-hydroxy-8-methoxy-1-methyl-tetralone-2 under nitrogen. Potassium ethoxide is added, and when reaction is complete, excess sulphuric acid 1-hydroxy-4-methoxy-7-keto-13-methyl-5 : 6 : 7 : 9 : 10 : 13-hexahydrophenanthrene is isolated with ether. A detailed description of the preparation of the various intermediates is also given.
GB24536/51A 1950-10-31 1951-10-22 Process for the preparation of intermediates in the synthesis of steroids and the products of such process Expired GB702012A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US702012XA 1950-10-31 1950-10-31

Publications (1)

Publication Number Publication Date
GB702012A true GB702012A (en) 1954-01-06

Family

ID=22093788

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24536/51A Expired GB702012A (en) 1950-10-31 1951-10-22 Process for the preparation of intermediates in the synthesis of steroids and the products of such process

Country Status (1)

Country Link
GB (1) GB702012A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111584012A (en) * 2020-04-17 2020-08-25 中国神华煤制油化工有限公司 Modeling method and control device for raw material reaction dynamics model

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111584012A (en) * 2020-04-17 2020-08-25 中国神华煤制油化工有限公司 Modeling method and control device for raw material reaction dynamics model
CN111584012B (en) * 2020-04-17 2023-10-03 中国神华煤制油化工有限公司 Modeling method and control device for raw material reaction kinetic model

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