IE35009L - 1,2-diphenyl-ethane derivatives - Google Patents

1,2-diphenyl-ethane derivatives

Info

Publication number
IE35009L
IE35009L IE710175A IE17571A IE35009L IE 35009 L IE35009 L IE 35009L IE 710175 A IE710175 A IE 710175A IE 17571 A IE17571 A IE 17571A IE 35009 L IE35009 L IE 35009L
Authority
IE
Ireland
Prior art keywords
general formula
alkyl group
hydrogen atom
reaction
formula above
Prior art date
Application number
IE710175A
Other versions
IE35009B1 (en
Original Assignee
Biorex Laboratories 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 Biorex Laboratories Ltd filed Critical Biorex Laboratories Ltd
Publication of IE35009L publication Critical patent/IE35009L/en
Publication of IE35009B1 publication Critical patent/IE35009B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • 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
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
    • 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
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions

Landscapes

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

Abstract

1280767 3,3<SP>1</SP> - Dihalo - 4,4<SP>1</SP> - dihydroxydibenzyls BIOREX LABORATORIES Ltd 19 April 1971 [16 March 1970] 12554/70 Heading C2C Novel 3,31 - dihalo - 4,4<SP>1</SP> - dihydroxydibenzyls of the general formula wherein R is a hydrogen atom or a C 1-6 alkyl or benzyl group, R 1 and R 2 are each a C 1-6 alkyl group, with the proviso that they are not both a methyl or ethyl group, and X is a halogen atom, are prepared (a) when R is a C 1-6 alkyl group, by hydrogenation of a diphenylethylene of the general formula wherein R<SP>11</SP> is a C 1-6 alkyl group; (b) when R is a hydrogen atom, by dealkylation of the corresponding compound in which R is an alkyl group; (c) when R is a C 1-6 alkyl group, by reaction of an ether of the general formula with a haloethanol of the general formula Hal-CH(R 1 )-CH(OH)R 2 , wherein Hal is a halogen atom; (d) when X is a chlorine or bromine atom and R is a hydrogen or C 1-6 alkyl group, by treatment of the corresponding compound in which X is a hydrogen atom with bromine, chlorine or sulphuryl chloride, as appropriate; (e) when R is a C 1-6 alkyl group, by reaction of a Grignard reagent and a benzyl halide of the resepctive general formulµ wherein R 3 is a C 3-6 alkyl group; (f) when R is a C 1-6 alkyl or benzyl group, by reaction of the corresponding compound in which R is a hydrogen atom with a C 1-6 alkyl or benzyl halide in the presence of an alkali metal hydroxide and an inert solvent; and (g) when R is a hydrogen atom, by hydrogenolysis of the corresponding compound in which R is a benzyl group. Diphenyl ethylenes of the second general formula above are prepared by reaction of an ether of the third general formula above with a ketone of the general formula 4,4<SP>1</SP>-Dihydroxydibenzyls of the first general formula above wherein X is a hydrogen atom and R is a hydrogen atom or C 1-6 alkyl group are prepared by reaction of an ether of the general formula with a ketone of the seventh general formula above, hydrogenation of the resulting diphenylethylene of the second general formula above wherein X is a hydrogen atom and optional dealkylation of the resulting desired product in which R is a C 1-6 alkyl group. Benzyl halides of the sixth general formula above are prepared by reaction of an ether of the third general formula above with an acid halide of the general formula R 3 COHal, reduction of the resulting ketone of the general formula and halogenation of the resulting alcohol of the general formula Pharmaceutical compositions having oestrogenic activity comprise, as active ingredient, at least one 3, 3<SP>1</SP>-dihalo-4,4<SP>1</SP>-dihydroxydibenzyl of the first general formula above, together with a solid or liquid pharmaceutical diluent or carrier, and may be administered orally. [GB1280767A]
IE175/71A 1970-03-16 1971-02-15 Derivatives of 1,2-diphenyl-ethane IE35009B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB02554/70A GB1280767A (en) 1970-03-16 1970-03-16 Derivatives of 1,2-diphenyl-ethane

Publications (2)

Publication Number Publication Date
IE35009L true IE35009L (en) 1971-09-16
IE35009B1 IE35009B1 (en) 1975-10-15

Family

ID=10006781

Family Applications (1)

Application Number Title Priority Date Filing Date
IE175/71A IE35009B1 (en) 1970-03-16 1971-02-15 Derivatives of 1,2-diphenyl-ethane

Country Status (18)

Country Link
JP (1) JPS515378B1 (en)
AT (1) AT303711B (en)
BE (1) BE764081A (en)
CA (1) CA948215A (en)
CH (1) CH558315A (en)
DK (1) DK146015C (en)
ES (1) ES389282A1 (en)
FI (1) FI55170C (en)
FR (1) FR2085710B1 (en)
GB (1) GB1280767A (en)
IE (1) IE35009B1 (en)
IL (1) IL36225A0 (en)
NL (1) NL146140B (en)
NO (1) NO132533C (en)
PH (1) PH10518A (en)
SE (1) SE393369B (en)
YU (1) YU35331B (en)
ZA (1) ZA71927B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5597271U (en) * 1978-12-28 1980-07-05

Also Published As

Publication number Publication date
FI55170C (en) 1979-06-11
FI55170B (en) 1979-02-28
SE393369B (en) 1977-05-09
CH558315A (en) 1975-01-31
JPS515378B1 (en) 1976-02-19
NO132533B (en) 1975-08-18
AT303711B (en) 1972-12-11
FR2085710A1 (en) 1971-12-31
YU53171A (en) 1980-06-30
NL7103249A (en) 1971-09-20
NO132533C (en) 1975-11-26
DK146015C (en) 1983-10-24
BE764081A (en) 1971-08-02
DE2110428B2 (en) 1976-08-26
IL36225A0 (en) 1971-04-28
YU35331B (en) 1980-12-31
GB1280767A (en) 1972-07-05
IE35009B1 (en) 1975-10-15
CA948215A (en) 1974-05-28
ES389282A1 (en) 1973-06-16
DE2110428A1 (en) 1971-10-07
NL146140B (en) 1975-06-16
FR2085710B1 (en) 1975-08-01
PH10518A (en) 1977-05-26
ZA71927B (en) 1971-10-27
DK146015B (en) 1983-05-24

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