Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation

被引：82

作者：

Bernini, Roberta ^{[1
]}

Mincione, Enrico ^{[1
]}

Barontini, Maurizio ^{[1
]}

Provenzano, Gianfranco ^{[1
]}

Setti, Leonardo ^{[2
]}

机构：

[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy

[2] Univ Bologna, Dipartimento Chim Ind & Mat, I-40136 Bologna, Italy

来源：

TETRAHEDRON | 2007年 / 63卷 / 39期

关键词：

D O I：

10.1016/j.tet.2007.07.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

4-Vinylphenols, useful compounds for industrial applications, were obtained by decarboxylation of 4-hydroxycinnamic acids under microwave irradiation in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base and basic aluminum oxide as solid support. The reactions were fast (15-0 min). The selective extraction of the final products with ethyl acetate avoids chromatographic purifications. The conversions are quantitative and the yields are satisfactory. Only the unstable 4-vinylcatechol was obtained in moderate yield. This procedure was successfully extended to a natural sample of ferulic acid extracted from wheat bran to get the corresponding 4-vinylguaiacol, a FEMA GRAS (Flavor and Extract Manufacturer's Association; General Regarded as Safe) approved flavoring agent. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：9663 / 9667

页数：5

共 53 条

[1]

AMES JM, 1990, PHYTOCHEMISTRY, V29, P1201, DOI 10.1016/0031-9422(90)85429-J

[2]

Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues [J].