公开(公告)号：US10266469B2

公开(公告)日：2019-04-23

申请号：US16079155

申请日：2017-02-16

申请人： BASF Agro B.V.

发明人： Bernd Wolf ,  Michael Rack ,  Stefan Benson ,  Roland Goetz ,  Helmut Kraus

IPC分类号： C07C35/18 ,  C07C29/17 ,  C07D303/04 ,  C07C35/00

摘要： The present invention relates to a process for preparing terpinene-4-ol from limonene-4-ol via a hydrogenation reaction in the presence of a nickel catalyst.

公开(公告)号：US11384093B2

公开(公告)日：2022-07-12

申请号：US16498625

申请日：2018-03-23

申请人： BASF Agro B.V.

发明人： Stefan Benson ,  Michael Rack ,  Christiane Alznauer ,  Roland Goetz ,  Bernd Wolf

IPC分类号： C07D493/08 ,  A01N25/02 ,  A01N43/90

摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso-propyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group, in the presence of at least one base, at least one catalyst selected from rubidium salts, cesium salts and any combination thereof and at least one inert organic solvent S1.

公开(公告)号：US11897895B2

公开(公告)日：2024-02-13

申请号：US16770969

申请日：2018-12-06

申请人： BASF AGRO B.V.

发明人： Michael Rack ,  Stefan Benson ,  Bernd Wolf ,  Roland Goetz

IPC分类号： C07D493/18

CPC分类号： C07D493/18

摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any one of its individual enantiomers or any non-racemic mixture thereof any one of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description) with elemental sodium to form a sodium salt of the formula (III), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description), and (b) reacting said sodium salt (III) with a 2-Methylbenzyl compound of the formula (IV) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one substantially anhydrous inert organic solvent.

公开(公告)号：US11639358B2

公开(公告)日：2023-05-02

申请号：US16614163

申请日：2018-05-09

申请人： BASF Agro B.V.

发明人： Klaus Ditrich ,  Michael Rack ,  Stefan Benson ,  Roland Goetz ,  Helmut Kraus

IPC分类号： C07D493/08

摘要： The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9% that have been prepared by this process. The present invention further relates to a process for preparing 7-oxabicyclo[2.2.1]heptane derivatives from the enantiomerically pure optically active 1,4-cineole derivatives.

公开(公告)号：US11866443B2

公开(公告)日：2024-01-09

申请号：US16614400

申请日：2018-05-09

申请人： BASF Agro B.V.

发明人： Klaus Ditrich ,  Michael Rack ,  Stefan Benson ,  Roland Goetz ,  Helmut Kraus

IPC分类号： C07D493/08 ,  C07B57/00

CPC分类号： C07D493/08 ,  C07B57/00 ,  C07B2200/07

摘要： The present invention relates to a method for separating an optically active hydroxy cineole derivatives by lixiviation and crystallization and enantiomerically pure optically active hydroxy cineole derivatives of purity greater than 99.5% that have been prepared by this process. The present invention further relates to use of the desired enantiomer having enantiomeric excess of at least 99.5% ee as prepared according to the present invention, for the synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]heptane derivatives.

公开(公告)号：US20220033411A1

公开(公告)日：2022-02-03

申请号：US16614163

申请日：2018-05-09

申请人： BASF Agro B.V.

发明人： Klaus Ditrich ,  Michael Rack ,  Stefan Benson ,  Roland Goetz ,  Helmut Kraus

IPC分类号： C07D493/08

摘要： The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9% that have been prepared by this process. The present invention further relates to a process for preparing 7-oxabicyclo[2.2.1]heptane derivatives from the enantiomerically pure optically active 1,4-cineole derivatives.

公开(公告)号：US10710969B2

公开(公告)日：2020-07-14

申请号：US16334152

申请日：2017-09-07

申请人： BASF Agro B.V.

发明人： Stefan Benson ,  Michael Rack ,  Bernd Wolf ,  Roland Goetz ,  Joachim Gebhardt ,  Helmut Kraus

IPC分类号： C07D307/00

摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1-C4 alkyl alcohol under the reaction conditions, and at least one inert organic solvent, and (b) simultaneously removing water, the C1-C4 alkyl alcohol or any mixture thereof from the reaction mixture.

公开(公告)号：US10538470B2

公开(公告)日：2020-01-21

申请号：US15571987

申请日：2016-04-22

申请人： BASF Agro B.V.

发明人： Bernd Wolf ,  Michael Rack ,  Stefan Benson ,  Helmut Kraus ,  Roland Goetz ,  Sukunath Narayanan ,  Chidambaram Rishinaradamangalam

IPC分类号： C07D307/00 ,  C07C29/56 ,  C07C29/17 ,  C07D493/08

摘要： The present invention relates to a process for the preparation of limonene-4-ol by an epoxide ring opening isomerization of terpinolene epoxide.

公开(公告)号：US11072593B2

公开(公告)日：2021-07-27

申请号：US16309478

申请日：2017-06-01

申请人： BASF Agro B.V.

发明人： Joachim Gebhardt ,  Michael Rack ,  Bernd Wolf ,  Stefan Benson ,  Roland Goetz ,  Helmut Kraus

IPC分类号： C07D301/16 ,  C07D303/04 ,  C07D493/08 ,  B01J19/00

摘要： This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with performic acid prepared in situ from formic acid and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and formic acid for the in-situ epoxidation of a tetrasubstituted alkene.

公开(公告)号：US20210163496A1

公开(公告)日：2021-06-03

申请号：US16770969

申请日：2018-12-06

申请人： BASF AGRO B.V.

发明人： Michael Rack ,  Stefan Benson ,  Bernd Wolf ,  Roland Goetz

IPC分类号： C07D493/18

摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any one of its individual enantiomers or any non-racemic mixture thereof any one of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description) with elemental sodium to form a sodium salt of the formula (III), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description), and (b) reacting said sodium salt (III) with a 2-Methylbenzyl compound of the formula (IV) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one substantially anhydrous inert organic solvent.