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F RIEDEL ‐C RAFTS ‐Reaktionen mit aromatischen äthern. 2. Mitteilung [1]. Reaktionsverlauf beim Umsatz von Veratrol mit Zimtsäure bzw. Zimtsäure‐methylester in Polyphosphorsäure
Author(s) -
Marquardt F.H.
Publication year - 1965
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19650480707
Subject(s) - chemistry , cinnamic acid , acylation , alkylation , propionate , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The condensation of cinnamic acid and veratrole, yielding 5, 6‐dimethoxy‐1‐indanone, takes place with acylation as the first step ( e.g. with 3′, 4′‐dimethoxy‐chalcone as intermediate), followed by alkylation. If the methyl ester of cinnamic acid is employed instead of the acid itself, the order of the steps is reversed ( e.g. with methyl β‐(3,4‐dimethoxyphenyl)‐β‐phenyl‐propionate as the main intermediate).