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 (15–30 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.

R. Bernini, E. Mincione, M. Barontini, G. Provengano, L. Setti (2007). Obtaining of 4-vinylphenols by decarboxylation of natural cinnamic acids under microwave irradiation. TETRAHEDRON, 63, 9663-9667 [10.1016/j.tet.2007.07.035].

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

SETTI, LEONARDO
2007

Abstract

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 (15–30 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.
2007
R. Bernini, E. Mincione, M. Barontini, G. Provengano, L. Setti (2007). Obtaining of 4-vinylphenols by decarboxylation of natural cinnamic acids under microwave irradiation. TETRAHEDRON, 63, 9663-9667 [10.1016/j.tet.2007.07.035].
R. Bernini; E. Mincione; M. Barontini; G. Provengano; L. Setti
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/54268
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