CONVENIENT SYNTHESIS OF BIPHENYL-2-CARBOXYLIC ACIDS VIA THE NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTION OF 2-METHOXYBENZOATES BY ARYL GRIGNARD-REAGENTS

被引：37

作者：

HATTORI, T

SUZUKI, T

HAYASHIZAKA, N

KOIKE, N

MIYANO, S

机构：

[1] TOHOKU UNIV, FAC ENGN, DEPT BIOCHEM & ENGN, AOBA KU, SENDAI, MIYAGI 980, JAPAN

[2] SUMITOMO SEIKA CHEM CO LTD, KYOGO 675011, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 10期

关键词：

D O I：

10.1246/bcsj.66.3034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic aromatic substitution (S(N)Ar) of 2-methoxybenzoic esters derived from 2,6-dialkylphenols by aryl Grignard reagents affords 1,1'-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2,6-dialkyl-substituents. The phenoxyl protecting groups can be easily removed from the resulting biphenyl-2-carboxylates to the free acids by treatment with potassium hydroxide in aqueous ethanol (2,4,6-trimethylphenyl and 2,6-diisopropylphenyl esters) or sodium methoxide in toluene-hexamethylphosphoric triamide (2,6-di-t-butyl-4-methylphenyl esters). The regioselective biphenyl coupling reaction via the SNAr process is utilized for the key-step construction of the biphenyl skeleton in a formal synthesis of cannabinol.

引用

页码：3034 / 3040

页数：7

共 38 条

[21] ASYMMETRIC CARBONYL ADDITION AND ASYMMETRIC POLYMERIZATION ASSISTED BY AXIALLY CHIRAL DIAMINES GIVE DISPARATE LIGAND PRODUCT CONFIGURATIONAL CORRELATIONS [J].