One-pot synthesis of ortho-hydroxycinnamate esters

被引：11

作者：

Anwar, HF

Skattebol, L

Skramstad, J

Hansen, TV

机构：

[1] Univ Oslo, Sch Pharm, Dept Chem, N-0316 Oslo, Norway

[2] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 32期

关键词：

ortho-hydroxycinnamate esters; ortho-formylation of phenols;

D O I：

10.1016/j.tetlet.2005.06.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl2-Et3N in THF, and subsequent treatment with methyl (triphenylphosphorinylidene)acetate gave the corresponding methyl ortho-hydroxycinnamate derivatives. The sequence is conveniently carried out as a one-pot procedure. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5285 / 5287

页数：3

相关论文

共 16 条

[1] A NEW SYNTHESIS OF ATRANOL (2,6-DIHYDROXY-4-METHYLBENZALDEHYDE) AND THE CORRESPONDING CINNAMIC ACID [J].

ADAMS, R ;

MATHIEU, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (06) :2120-2122

[2]

ADAMS R, 1954, J AM CHEM SOC, V75, P5346

[3] Preparation of cinnamate esters from styrenes [J].

Aslam, M ;

Stansbury, WF ;

Reiter, RJ ;

Larkin, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1550-1552

[4] Synthesis of coumarins by flash vacuum pyrolysis of 3-(2-hydroxyaryl)propenoic esters [J].

Cartwright, GA ;

McNab, H .

JOURNAL OF CHEMICAL RESEARCH-S, 1997, (08) :296-297

[5] SIDE REACTIONS IN THE PHASE-TRANSFER CATALYZED WITTIG-HORNER SYNTHESIS - A CONVENIENT METHOD OF PREPARATION OF HYDROXYCINNAMIC ACIDS [J].

CHENAULT, J ;

DUPIN, JFE .

SYNTHETIC COMMUNICATIONS, 1984, 14 (11) :1059-1065

[6] PHASE-TRANSFER CATALYZED WITTIG-HORNER SYNTHESIS PREPARATION OF HYDROXYCINNAMIC ESTERS FROM ORTHO HYDROXY AROMATIC-ALDEHYDES OBTENTION OF HYDROXYCINNAMIC ACIDS [J].

DUPIN, JFE ;

CHENAULT, J .

SYNTHETIC COMMUNICATIONS, 1985, 15 (07) :581-586

[7] A high yielding one-pot method for the preparation of salen ligands [J].

Hansen, TV ;

Skattebol, L .

TETRAHEDRON LETTERS, 2005, 46 (22) :3829-3830

[8] One-pot synthesis of substituted catechols from the corresponding phenols [J].

Hansen, TV ;

Skattebol, L .

TETRAHEDRON LETTERS, 2005, 46 (19) :3357-3358

[9] Convenient method for the ortho-formylation of phenols [J].

Hofslokken, NU ;

Skattebol, L .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (04) :258-262

[10]

JOHNSON JR, 1942, PERKIN REACTION RELA, V1, P218