DE102004036068A1 - Disubstituted cyclohexane or tetrahydropyran derivative preparation, for use e.g. in liquid crystals, by trans-selective hydrogenation of cyclohexene or dihydropyran derivative over transition metal phosphine complex - Google Patents

Disubstituted cyclohexane or tetrahydropyran derivative preparation, for use e.g. in liquid crystals, by trans-selective hydrogenation of cyclohexene or dihydropyran derivative over transition metal phosphine complex Download PDF

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Publication number
DE102004036068A1
DE102004036068A1 DE102004036068A DE102004036068A DE102004036068A1 DE 102004036068 A1 DE102004036068 A1 DE 102004036068A1 DE 102004036068 A DE102004036068 A DE 102004036068A DE 102004036068 A DE102004036068 A DE 102004036068A DE 102004036068 A1 DE102004036068 A1 DE 102004036068A1
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oco
coo
optionally
direct bond
replaced
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DE102004036068A
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DE102004036068B4 (en
Inventor
Joachim Kralik
Christoph Muermann
Stefan Lehmann
Eike Poetsch
Volker Meyer
Werner Binder
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Merck Patent GmbH
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Merck Patent GmbH
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    • 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
    • C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D309/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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

Abstract

Production of 1,4-disubstituted cyclohexane or 2,5-disubstituted tetrahydropyran derivatives (I) involves hydrogenating a corresponding cyclohexene or dihydropyran derivative (II) in presence of a transition metal complex (III) stabilized by one or more same or different phosphine ligands. Production of cyclohexane or tetrahydropyran derivatives (I) of formula (IA) or (IB) involves hydrogenating a corresponding cyclohexene or dihydropyran derivative (II) of formula (IIA) or (IIB) in presence of a transition metal complex (III) stabilized by one or more same or different phosphine ligands. [Image] [Image] W : O or CH 2; a - e and f - j : 0 or 1, provided that e and j = 1 if W = CH 2; A 1>1>- A 1>5>, A 2>1>- A 2>5>1,4-cyclohexylene (in which 1 or 2 non-adjacent CH 2groups are optionally replaced by O and/or S), 1,4-phenylene (in which 1 or 2 non-adjacent CH groups are optionally replaced by N), naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl (all optionally substituted (os) by one or more of halo or CN); or 1,3-cyclobutylene, piperidine-1,4-diyl or decahydronaphthalene-2,6-diyl; R 1>1>H or 1-15C alkyl (os and optionally having one or more CH 2groups replaced by CC, S, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked), provided that R 1>1>is not H if a = b = 0 and Z 1>2>= direct bond; R 2>1>H or 1-15C alkyl (os and optionally having one or more CH 2groups replaced by CH=CH, CC, S, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked), provided that R 2>1>is not H if f = g = 0 and Z 2>2>= direct bond; Y 1>1>H, halo, NCS, SCN, SF 6or CN; or 1-15C alkyl (os by one or more of halo or CN) or 7-16C aralkyl (os by one or more of halo, NO 2, alkanoyl, alkoxy, NH 2or dialkanoylamino) (both optionally having one or more CH 2groups replaced by CC, S, SO, SO 2, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked); Y 2>1>H, halo, NCS, SCN, SF 6or CN; or os 1-15C alkyl or 7-16C aralkyl (both optionally having one or more CH 2groups replaced by CH=CH, CC, S, SO, SO 2, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked); Z 1>1>, Z 1>3>- Z 1>5>direct bond, CH 2CH 2, CF 2CF 2, CHCF 2, CF 2CH 2, CHFCHF, CC, CH 2O, OCH 2, CF 2O, OCF 2, COO or OCO; Z 2>1>, Z 2>3>- Z 2>5>direct bond, CH=CH, CH 2CH 2, CF 2CF 2, CHCF 2, CF 2CH 2, CHFCHF, CC, CH 2O, OCH 2, CF 2O, OCF 2, COO or OCO; Z 1>2>direct bond, CH 2CH 2, CC, CH 2O, OCH 2, COO or OCO; Z 2>2>direct bond, CH=CH, CH 2CH 2, CC, CH 2O, OCH 2, COO or OCO. An independent claim is included for compositions comprising a compound (II) and at least one of the stabilized complexes (III).
DE102004036068.5A 2003-08-18 2004-07-24 Process for hydrogenation Active DE102004036068B4 (en)

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DE102004036068.5A DE102004036068B4 (en) 2003-08-18 2004-07-24 Process for hydrogenation

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DE10337836.7 2003-08-18
DE10337836 2003-08-18
DE102004036068.5A DE102004036068B4 (en) 2003-08-18 2004-07-24 Process for hydrogenation

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DE102004036068B4 DE102004036068B4 (en) 2023-05-17

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
US9422477B2 (en) 2014-10-29 2016-08-23 Samsung Display Co., Ltd. Liquid crystal compositon and liquid crystal display including the same
US9567525B2 (en) 2015-04-30 2017-02-14 Samsung Display Co., Ltd. Liquid crystal composition, liquid crystal display including the same and method of manufacturing thereof
US11884862B2 (en) 2015-08-05 2024-01-30 Merck Patent Gmbh Liquid-crystalline medium

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KR101393783B1 (en) * 2005-05-25 2014-05-14 메르크 파텐트 게엠베하 Method for producing 2,5-substituted tetrahydropyran derivatives by reductive elimination of the corresponding 4-halogen derivative
KR101307666B1 (en) * 2005-05-25 2013-09-16 메르크 파텐트 게엠베하 Method for producing tetrahydropyran derivatives
JP6627515B2 (en) * 2015-02-06 2020-01-08 Jnc株式会社 Liquid crystal compound having negative dielectric anisotropy having 3,6-dihydro-2H-pyran, liquid crystal composition, and liquid crystal display device

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9422477B2 (en) 2014-10-29 2016-08-23 Samsung Display Co., Ltd. Liquid crystal compositon and liquid crystal display including the same
US9567525B2 (en) 2015-04-30 2017-02-14 Samsung Display Co., Ltd. Liquid crystal composition, liquid crystal display including the same and method of manufacturing thereof
US11884862B2 (en) 2015-08-05 2024-01-30 Merck Patent Gmbh Liquid-crystalline medium

Also Published As

Publication number Publication date
KR20050020947A (en) 2005-03-04
JP4854941B2 (en) 2012-01-18
CN1626492A (en) 2005-06-15
DE102004036068B4 (en) 2023-05-17
CN1626492B (en) 2010-05-26
JP2005060399A (en) 2005-03-10
KR101161870B1 (en) 2012-07-02

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