Method for producing substituted 1.4 chinonmethides
Preparing (M1) a substituted 1,4-quinone methide (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde (II) with an orthoformate (III) and an alcohol and/or thioalcohol ((thio)alcohol) (IV) in the presence of at least one catalyst e.g. free or solid-phase-bound organic sulfonic acid, sulfu...
Saved in:
Main Authors | , , , , |
---|---|
Format | Patent |
Language | English French German |
Published |
07.06.2017
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | Preparing (M1) a substituted 1,4-quinone methide (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde (II) with an orthoformate (III) and an alcohol and/or thioalcohol ((thio)alcohol) (IV) in the presence of at least one catalyst e.g. free or solid-phase-bound organic sulfonic acid, sulfuric acid, a hydrogen sulfate, an organic or inorganic phosphorus acid, fuming nitric acid and boric acid, to obtain a (thio)acetal; and eliminating the alcohol or thiol from the obtained (thio)acetal to form substituted 1,4-quinone methide (I). Preparing (M1) a substituted 1,4-quinone methide of formula (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde of formula (II) with an orthoformate of formula R 6O-CH(OR 4)-OR 5(III) and an alcohol and/or thioalcohol ((thio)alcohol) of formula R 3-X-H (IV) in the presence of a at least one catalyst selected from a free or solid-phase-bound organic sulfonic acid, sulfuric acid, a hydrogensulfate, an organic or inorganic phosphorus acid, a dihydrogen or hydrogen salt of an organic or inorganic phosphorous acid, fuming nitric acid and boric acid, to obtain a (thio)acetal; and eliminating the alcohol or thiol from the obtained (thio)acetal to form the substituted 1,4-quinone methide (I). R 1and R 2 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted) or H; R 7 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted); X : O or S; R 4, R 5and R 6 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted); R 3 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted). Independent claims are included for following: (1) preparing a substituted 1,4-quinone methide of formula (V) involving reacting a substituted 1,4-quinone methide (I) (R 7is unsubstituted 1-2C alkyl and X is O) with an alcohol or thioalcohol of formula R 8-SH (VI) to form substituted 1,4-quinone methide of formula (V); and (2) preparing (M2) a 3,5-disubstituted 4-hydroxybenzaldehyde (II) involving reacting a 2,6-disubstituted phenol of formula (VII) with urotropin in a solvent mixture consisting of glacial acetic acid and water at temperature of at least 2[deg] C below a reflux temperature of the reaction mixture over the entire reaction time. R 8 : 3-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted). [Image] [Image]. |
---|---|
AbstractList | Preparing (M1) a substituted 1,4-quinone methide (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde (II) with an orthoformate (III) and an alcohol and/or thioalcohol ((thio)alcohol) (IV) in the presence of at least one catalyst e.g. free or solid-phase-bound organic sulfonic acid, sulfuric acid, a hydrogen sulfate, an organic or inorganic phosphorus acid, fuming nitric acid and boric acid, to obtain a (thio)acetal; and eliminating the alcohol or thiol from the obtained (thio)acetal to form substituted 1,4-quinone methide (I). Preparing (M1) a substituted 1,4-quinone methide of formula (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde of formula (II) with an orthoformate of formula R 6O-CH(OR 4)-OR 5(III) and an alcohol and/or thioalcohol ((thio)alcohol) of formula R 3-X-H (IV) in the presence of a at least one catalyst selected from a free or solid-phase-bound organic sulfonic acid, sulfuric acid, a hydrogensulfate, an organic or inorganic phosphorus acid, a dihydrogen or hydrogen salt of an organic or inorganic phosphorous acid, fuming nitric acid and boric acid, to obtain a (thio)acetal; and eliminating the alcohol or thiol from the obtained (thio)acetal to form the substituted 1,4-quinone methide (I). R 1and R 2 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted) or H; R 7 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted); X : O or S; R 4, R 5and R 6 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted); R 3 : 1-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted). Independent claims are included for following: (1) preparing a substituted 1,4-quinone methide of formula (V) involving reacting a substituted 1,4-quinone methide (I) (R 7is unsubstituted 1-2C alkyl and X is O) with an alcohol or thioalcohol of formula R 8-SH (VI) to form substituted 1,4-quinone methide of formula (V); and (2) preparing (M2) a 3,5-disubstituted 4-hydroxybenzaldehyde (II) involving reacting a 2,6-disubstituted phenol of formula (VII) with urotropin in a solvent mixture consisting of glacial acetic acid and water at temperature of at least 2[deg] C below a reflux temperature of the reaction mixture over the entire reaction time. R 8 : 3-15C alkyl, 3-15C cycloalkyl or 6-14C aryl (all optionally substituted). [Image] [Image]. |
Author | Rinker, Stefanie, Dr Kraushaar, Frank, Dr Erpeldinger, Oliver Neumann, Manfred, Dr James, Phillip, R., Dr |
Author_xml | – fullname: Rinker, Stefanie, Dr – fullname: Erpeldinger, Oliver – fullname: Kraushaar, Frank, Dr – fullname: Neumann, Manfred, Dr – fullname: James, Phillip, R., Dr |
BookMark | eNrjYmDJy89L5WQw9k0tychPUUjLL1IoKMpPKU3OzEtXKC5NKi7JLCktSU1RMNQzUUjOyAQqzwUqzUxJLeZhYE1LzClO5YXS3AwKbq4hzh66qQX58anFBYnJqXmpJfGuAUZGJsbmZiZOhsZEKAEAlootsg |
ContentType | Patent |
DBID | EVB |
DatabaseName | esp@cenet |
DatabaseTitleList | |
Database_xml | – sequence: 1 dbid: EVB name: esp@cenet url: http://worldwide.espacenet.com/singleLineSearch?locale=en_EP sourceTypes: Open Access Repository |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Medicine Chemistry Sciences |
DocumentTitleAlternate | Procédé de fabrication de 1,4-quinone méthides substitués Verfahren zur Herstellung von substituierten 1,4-Chinonmethiden |
ExternalDocumentID | EP2243764B1 |
GroupedDBID | EVB |
ID | FETCH-epo_espacenet_EP2243764B13 |
IEDL.DBID | EVB |
IngestDate | Fri Jul 19 14:54:10 EDT 2024 |
IsOpenAccess | true |
IsPeerReviewed | false |
IsScholarly | false |
Language | English French German |
LinkModel | DirectLink |
MergedId | FETCHMERGED-epo_espacenet_EP2243764B13 |
Notes | Application Number: EP20100157058 |
OpenAccessLink | https://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20170607&DB=EPODOC&CC=EP&NR=2243764B1 |
ParticipantIDs | epo_espacenet_EP2243764B1 |
PublicationCentury | 2000 |
PublicationDate | 20170607 |
PublicationDateYYYYMMDD | 2017-06-07 |
PublicationDate_xml | – month: 06 year: 2017 text: 20170607 day: 07 |
PublicationDecade | 2010 |
PublicationYear | 2017 |
RelatedCompanies | Evonik Degussa GmbH |
RelatedCompanies_xml | – name: Evonik Degussa GmbH |
Score | 3.0825534 |
Snippet | Preparing (M1) a substituted 1,4-quinone methide (I) involves reacting a 3,5-disubstituted 4-hydroxybenzaldehyde (II) with an orthoformate (III) and an alcohol... |
SourceID | epo |
SourceType | Open Access Repository |
SubjectTerms | ACYCLIC OR CARBOCYCLIC COMPOUNDS CHEMISTRY METALLURGY ORGANIC CHEMISTRY |
Title | Method for producing substituted 1.4 chinonmethides |
URI | https://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20170607&DB=EPODOC&locale=&CC=EP&NR=2243764B1 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT8MwDLamgYAbDBDjpRxQbwWatMt6qJD60oTUrUID7TY1bSp2GRUN4u_jhG5wgVuUKA9HcmzH9meAG128gUq3tEtRoYHiOLU9rvi9rUtw88IXbCx1vnM2HU2e3ceFt-jBapMLY3BCPw04InJUifyuzHvd_HxixSa2sr0TK-x6e0jnQWx11rHBguFWHAZJPotnkRVF2LKmTwHVwHsjN0RDaUdr0RpmP3kJdVJK81uipIewm-Nia3UEvUoOYD_aFF4bwF7W-bux2bFeewwsM7WeCSqZpDEwrSh0SIt8_-3sr4hz6xIdGanT1tQrEteeAEmTeTSxcfflltJlkm_PyU6hjxPkGRDOas5QTBcabozSwmeS-p5fU18UvPLEEIZ_LnP-z9gFHOgrM4FP_BL66v1DXqGIVeLaXM4XmRR_ig |
link.rule.ids | 230,309,786,891,25594,76906 |
linkProvider | European Patent Office |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT8MwDLamgRg3GCDGMwfUW4Gm7bIeKqS-VGDtKlTQblWzttouUNEi_j5O6AYXuEWJ8nAkx3Zsfwa4EsUbaGks1AUv0EDRtEqdFOxWFSW4WW5xfVKKfOcoHofPxsPcnPdgtc6FkTihnxIcETlqgfzeyve6_vnE8mRsZXPDV9j1dhektqd01rHEgmGK59h-MvNmruK62FLiJ5sK4L2x4aChtMUEOK_QnF4ckZRS_5YowR5sJ7jYa7sPvaIcwsBdF14bwk7U-bux2bFecwB6JGs9E1QySS1hWlHokAb5_tvZXxDt2iAiMlKkrbVLJK45BBL4qRuquHu2oTTzk8059SPo44TyGAjTK6ajmM4F3BiluaWX1DKtilo8Z4XJRzD6c5mTf8YuYRCm0TSb3sePp7Arrk8GQbEz6LfvH-U5ituWX8iL-gK3_oJ3 |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.title=Method+for+producing+substituted+1.4+chinonmethides&rft.inventor=Rinker%2C+Stefanie%2C+Dr&rft.inventor=Erpeldinger%2C+Oliver&rft.inventor=Kraushaar%2C+Frank%2C+Dr&rft.inventor=Neumann%2C+Manfred%2C+Dr&rft.inventor=James%2C+Phillip%2C+R.%2C+Dr&rft.date=2017-06-07&rft.externalDBID=B1&rft.externalDocID=EP2243764B1 |