Title:
２，６－ジアルキルフェニル酢酸の製造方法
Document Type and Number:
Japanese Patent JP7353295
Kind Code:
B2
Abstract:
The invention relates to a multi-stage process for preparing 2,6-dialkylphenylacetic acids of the general formula (I) by reacting 2,6-dialkylbromobenzenes with (1) magnesium, (2) a formamide, (3) an acid, (4) hydrogenation of the benzaldehyde obtained, (5) activation of the benzyl alcohol obtained, (6) cyanation of the activated benzyl alcohol and (7) hydrolysis of the nitrile obtained.
Inventors:
Himler, Thomas
Brome, dirk
Moradi, Wahed Ahmed
Brome, dirk
Moradi, Wahed Ahmed
Application Number:
JP2020555161A
Publication Date:
September 29, 2023
Filing Date:
April 03, 2019
Export Citation:
Assignee:
Bayer Actien Gezershyaft
International Classes:
B01J25/00; C07C51/08; C07C29/141; C07C33/30; C07C57/30; C07C57/58; C07C309/65; C07C309/66; C07C309/73; C07F3/02
Domestic Patent References:
| JP2002513025A | ||||
| JP2011512321A | ||||
| JP2010235603A | ||||
| JP2003510326A | ||||
| JP2014525401A | ||||
| JP2007031430A | ||||
| JP2001158754A | ||||
| JP58067637A | ||||
| JP8225467A | ||||
| JP2007536338A |
Foreign References:
| WO2006011670A1 | ||||
| US20110039701 | ||||
| WO2016071920A2 | ||||
| WO2017121699A1 | ||||
| WO2018015489A1 | ||||
| WO2016193761A1 |
Other References:
XIANG L; ET AL,STEREOSELECTIVE SYNTHESIS OF ALL INDIVIDUAL ISOMERS OF [BETA]-METHYL-2',6'-DIMETHYLPHENYLALANINE,TETRAHEDRON ASYMMETRY,英国,PERGAMON PRESS LTD,1995年,VOL:6, NR:1,PAGE(S):83 - 86,http://dx.doi.org/10.1016/0957-4166(94)00357-H
Zhu, Chunlan et al,Synthesis of 2,4,6-trimethylbenzaldehyde,Jingxi Huagong Zhongjianti ,2005年,35(3),,33-34
STN Interntional, file CHEMCATS,2017年12月17日,CAS Registry No. 2159586-57-7,化合物名Benzenemethanol, 2, 6-dimethyl-, 1-(4-methylbenzenesulfonate)
STN Interntional, file CHEMCATS,2014年05月09日,CAS Registry No. 1601046-43-8,化合物名Benzenemethanol, 2, 4, 6-trimethyl-, 1-methanesulfonate
STN Interntional, file CHEMCATS,2016年02月26日,CAS Registry No. 1874998-32-9,化合物名Methanesulfonic acid, 1,1,1-trifluoro-, (2,4,6-trimethylphenyl)methylester
STN Interntional, file CHEMCATS,2016年03月04日,CAS Registry No. 1879859-20-7,化合物名Methanesulfonic acid, 1, 1, 1-trifluoro-, (2, 6-dimethylphenyl) methyl ester
LOFGREN NILS; ET AL,SYNTHESES OF THREE XYLOCAINE(R) ANALOGUES STERIC EFFECTS IN THE REACTION BETWEEN 以下備考,ACTA CHEMICA SCANDINAVICA,デンマーク,1963年,VOL:17,NR:5,PAGE(S):1252 - 1261,http://dx.doi.org/10.3891/acta.chem.scand.17-1252,2,6-DIMETHYLPHENYLLITHIUM AND EPICHLOROHYDRIN
Wei, Yingfei et al,Synthesis of Triazolylidene Nickel Complexes and Their Catalytic Application in Selective Aldehyde Hydrosilylation,ACS Catalysis,2016年,6(12),,8192-8200
Bui The Khai; Arcelli, Antonio,Selective reduction of aldehydes by a formic acid-trialkylamine-dichlorotris(triphenylphosphine)ruthenium [RuCl2(PPh3)3] system,Tetrahedron Letters ,1985年,26(28),,3365-8
Delgado-Rebollo, Manuela et al,Synthesis and catalytic alcohol oxidation and ketone transfer hydrogenation activity of donor-functionalized mesoionic triazolylidene ruthenium(ii) complexes,Dalton Transactions ,2014年,43(11),,4462-4473
Sommer, Michael G. et al,Ruthenium Azocarboxamide Half-Sandwich Complexes: Influence of the Coordination Mode on the Electronic Structure and Activity in Base-Free Transfer Hydrogenation Catalysis,Organometallics,2016年,35(17),,2840-2849
Collier, Steven J.,2-Propanol,e-EROS Encyclopedia of Reagents for Organic Synthesis,2016年,1-15
GEIER G R; ET AL,EFFECTS OF ALDEHYDE OR DIPYRROMETHANE SUBSTITUENTS ON THE REACTION COURSE LEADING 以下備考,TETRAHEDRON,2004年10月18日,VOL:60, NR:50,PAGE(S):11435 - 11444, S1 - S29,http://dx.doi.org/10.1016/j.tet.2004.09.081,TO MESO-SUBSTITUTED PORPHYRINS
Zhu, Chunlan et al,Synthesis of 2,4,6-trimethylbenzaldehyde,Jingxi Huagong Zhongjianti ,2005年,35(3),,33-34
STN Interntional, file CHEMCATS,2017年12月17日,CAS Registry No. 2159586-57-7,化合物名Benzenemethanol, 2, 6-dimethyl-, 1-(4-methylbenzenesulfonate)
STN Interntional, file CHEMCATS,2014年05月09日,CAS Registry No. 1601046-43-8,化合物名Benzenemethanol, 2, 4, 6-trimethyl-, 1-methanesulfonate
STN Interntional, file CHEMCATS,2016年02月26日,CAS Registry No. 1874998-32-9,化合物名Methanesulfonic acid, 1,1,1-trifluoro-, (2,4,6-trimethylphenyl)methylester
STN Interntional, file CHEMCATS,2016年03月04日,CAS Registry No. 1879859-20-7,化合物名Methanesulfonic acid, 1, 1, 1-trifluoro-, (2, 6-dimethylphenyl) methyl ester
LOFGREN NILS; ET AL,SYNTHESES OF THREE XYLOCAINE(R) ANALOGUES STERIC EFFECTS IN THE REACTION BETWEEN 以下備考,ACTA CHEMICA SCANDINAVICA,デンマーク,1963年,VOL:17,NR:5,PAGE(S):1252 - 1261,http://dx.doi.org/10.3891/acta.chem.scand.17-1252,2,6-DIMETHYLPHENYLLITHIUM AND EPICHLOROHYDRIN
Wei, Yingfei et al,Synthesis of Triazolylidene Nickel Complexes and Their Catalytic Application in Selective Aldehyde Hydrosilylation,ACS Catalysis,2016年,6(12),,8192-8200
Bui The Khai; Arcelli, Antonio,Selective reduction of aldehydes by a formic acid-trialkylamine-dichlorotris(triphenylphosphine)ruthenium [RuCl2(PPh3)3] system,Tetrahedron Letters ,1985年,26(28),,3365-8
Delgado-Rebollo, Manuela et al,Synthesis and catalytic alcohol oxidation and ketone transfer hydrogenation activity of donor-functionalized mesoionic triazolylidene ruthenium(ii) complexes,Dalton Transactions ,2014年,43(11),,4462-4473
Sommer, Michael G. et al,Ruthenium Azocarboxamide Half-Sandwich Complexes: Influence of the Coordination Mode on the Electronic Structure and Activity in Base-Free Transfer Hydrogenation Catalysis,Organometallics,2016年,35(17),,2840-2849
Collier, Steven J.,2-Propanol,e-EROS Encyclopedia of Reagents for Organic Synthesis,2016年,1-15
GEIER G R; ET AL,EFFECTS OF ALDEHYDE OR DIPYRROMETHANE SUBSTITUENTS ON THE REACTION COURSE LEADING 以下備考,TETRAHEDRON,2004年10月18日,VOL:60, NR:50,PAGE(S):11435 - 11444, S1 - S29,http://dx.doi.org/10.1016/j.tet.2004.09.081,TO MESO-SUBSTITUTED PORPHYRINS
Attorney, Agent or Firm:
Makoto Ono
Kennori Kanayama
Yoshiyuki Tsubokura
Kazuki Shigemori
Kenji Ando
Hidehiko Ichikawa
Yoshie Sakurada
Yosuke Kawasaki
Takuya Gomibuchi
Youichi Iino
Yusuke Ichikawa
Masahiro Moriyama
Takashi Kawano
Yoshikazu Iwase
Yasufumi Shiroyama
Kennori Kanayama
Yoshiyuki Tsubokura
Kazuki Shigemori
Kenji Ando
Hidehiko Ichikawa
Yoshie Sakurada
Yosuke Kawasaki
Takuya Gomibuchi
Youichi Iino
Yusuke Ichikawa
Masahiro Moriyama
Takashi Kawano
Yoshikazu Iwase
Yasufumi Shiroyama