GB537976A - A process for the preparation of di-phenyl ethylene derivatives - Google Patents

A process for the preparation of di-phenyl ethylene derivatives

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Publication number
GB537976A
GB537976A GB32421/39A GB3242139A GB537976A GB 537976 A GB537976 A GB 537976A GB 32421/39 A GB32421/39 A GB 32421/39A GB 3242139 A GB3242139 A GB 3242139A GB 537976 A GB537976 A GB 537976A
Authority
GB
United Kingdom
Prior art keywords
dehydration
phosphorus
ethylene
alkyl
migration
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
GB32421/39A
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB537976A publication Critical patent/GB537976A/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
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • 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
    • 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
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings

Landscapes

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

Abstract

537,976. Di-phenyl ethane derivatives. CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA, R. T. (DR. KERESZTY & DR. WOLF). Dec. 18, 1939, Nos. 32421 and 32422. Convention dates, Jan. 5 and Feb. 7. [Class 2 (iii)] Diphenylethane derivatives having oestrogenic activity are prepared by subjecting compounds of the general formula where X may be hydrogen alkyl or aralkyl, and where the benzene ring may be further substituted to the action of an alkyl magnesium halide to produce an alcohol of the formula which is then dehydrated to produce the ethylene compound. This dehydration may be carried out by direct removal of water such as by using an alcoholic solution of a hydrogen halide or by replacing the hydroxyl group by chlorine by the action of phosphorus halogenides followed by removal of hydrogen halide. The first method of dehydration involves little or no migration of the benzene nuclei and the product obtained accordingly consists almost entirely of α-α di-alkyl-##-diaryl ethylene. The second method of dehydration particularly when phosphorus oxy-chloride is used, involves considerable migration to give a considerable amount of α#-di-alkyl-α#-diaryl ethylene. If desired the ethylene compound may be subjected to a desalkylation treatment with alcoholic alkali solution at . elevated temperature. Phosphorus pentabromide may also be used instead of phosphorus oxychloride as halogenating agent in the second method of dehydration. The withdrawal of hydrogen halide may be effected by means of alcoholic alkali, or with a tertiary amine such as pyridine or by boiling in a solvent such as toluene above 100‹ C. In the preferred form of the invention the starting material is chlorodesoxyarisoin or another halogeno-desoxy anisoin. These compounds may be obtained by the action of phosphorus halogenides on the benzoins. As alkyl magnesium halides, methyl magnesium bromide and iodide, ethyl-, propyl-, and isoamyl-magnesium bromides may be used. In an example chloro-desoxy anisoin is added to an ethereal solution of ethyl magnesium bromide to give αα-diethyl-##-dianisylethanol which is then dehydrated by heating with dilute sulphuric acid at 70‹-95‹ C. under 0.001 mm. pressure to form αα-diethyl-##- dianisyl ethylene. The dehydration may also be carried out by heating the ethanol with phosphorus oxychloride and boiling the halogenide with toluene. In this case considerable migration takes place to give α#-diethyl-α#- dianisyl ethylene. Another method for carrying out the dehydration with migration is to treat the ethanol with phosphorus pentabromide and then to remove hydrogen halide with either alcoholic potassium hydroxide or pyridine.
GB32421/39A 1939-01-05 1939-12-18 A process for the preparation of di-phenyl ethylene derivatives Expired GB537976A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU537976X 1939-01-05

Publications (1)

Publication Number Publication Date
GB537976A true GB537976A (en) 1941-07-16

Family

ID=10979544

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32421/39A Expired GB537976A (en) 1939-01-05 1939-12-18 A process for the preparation of di-phenyl ethylene derivatives

Country Status (1)

Country Link
GB (1) GB537976A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2779800A (en) * 1954-11-30 1957-01-29 Shell Dev Process for the production of poly-(hydroxyaryl) alkane compounds and new products thereof
US3237200A (en) * 1959-02-25 1966-02-22 Barany Ernst Herbert Carboxylic acid esters
US3287397A (en) * 1960-11-22 1966-11-22 Olsson Knut Gunnar P, p' substituted benzhydrylidine cycloalkanes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2779800A (en) * 1954-11-30 1957-01-29 Shell Dev Process for the production of poly-(hydroxyaryl) alkane compounds and new products thereof
US3237200A (en) * 1959-02-25 1966-02-22 Barany Ernst Herbert Carboxylic acid esters
US3287397A (en) * 1960-11-22 1966-11-22 Olsson Knut Gunnar P, p' substituted benzhydrylidine cycloalkanes

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