GB596957A - A process for the manufacture of diaryl-dialkyl-ethane derivatives - Google Patents

A process for the manufacture of diaryl-dialkyl-ethane derivatives

Info

Publication number
GB596957A
GB596957A GB20224/45A GB2022445A GB596957A GB 596957 A GB596957 A GB 596957A GB 20224/45 A GB20224/45 A GB 20224/45A GB 2022445 A GB2022445 A GB 2022445A GB 596957 A GB596957 A GB 596957A
Authority
GB
United Kingdom
Prior art keywords
dialkyl
hydroxyphenyl
stilbenequinones
butadienes
diethyl
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
GB20224/45A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB596957A publication Critical patent/GB596957A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • 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
    • C07C37/003—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 hydrogenation of an unsaturated part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring

Landscapes

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

Abstract

1 : 2 - Di - (p - hydroxyphenyl) - 1 : 2 - dialkyl - ethanes are produced by oxidizing 1 : 2-di-(p-hydroxyphenyl) - 1 : 2 - dialkylethylenes with mild oxidizing agents, e.g. PbO2, FeCl3, Ag2O and lead tetracetate, rearranging the a ,b -dialkyl-stilbenequinones, by treatment with an acid (e.g. a concentrated organic acid or dilute mineral acid) or alkali, into 2 : 3-di-(p-hydroxyphenyl)-butadienes-1 : 3, which are substituted or unsubstituted in the 1 and/or 4 positions, and reducing said butadienes, e.g. by hydrogen iodide in the presence of phosphorus or by catalytic hydrogenation using palladium. In an example, diethyl-stilboestrol is oxidized to a : b - diethyl - stilbenequinone which is rearranged into isodiene-oestrol and reduced to 1 : 2-di-(p-hydroxyphenyl)-1 : 2-diethylethane. The Specification as open to inspection under Sect. 91 comprises also the direct hydrogenation of the a ,b -dialkyl stilbenequinones in the presence of platinum to produce trans-1 : 2-di-(p-hydroxy - phenyl) - 1 : 2-dialkyl - ethylenes, thus making it possible to convert the cis-compounds into the corresponding trans-compounds. This subject-matter does not appear in the Specification as accepted.
GB20224/45A 1944-08-23 1945-08-07 A process for the manufacture of diaryl-dialkyl-ethane derivatives Expired GB596957A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE596957X 1944-08-23

Publications (1)

Publication Number Publication Date
GB596957A true GB596957A (en) 1948-01-14

Family

ID=20312745

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20224/45A Expired GB596957A (en) 1944-08-23 1945-08-07 A process for the manufacture of diaryl-dialkyl-ethane derivatives

Country Status (1)

Country Link
GB (1) GB596957A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960931A (en) * 1973-03-23 1976-06-01 Biorex Laboratories, Limited 1,2-Diphenyl-ethane derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960931A (en) * 1973-03-23 1976-06-01 Biorex Laboratories, Limited 1,2-Diphenyl-ethane derivatives

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