Abstract
A mixture of dehydroabietic acid (DHAA, RCOOH), phenol, and phosphoryl chloride was heated to give phenyl dehydroabietate in 83 % yield. In the reactions of cresols with DHAA under the same conditions, the yields of tolyl dehydroabietates increased with in the distance between methyl and hydroxyl group.
p- MeC6H4O (O) CR> m-MeC6H4O (O) CR> o- MeC6H4O (O) CR
In the reactions of o-cresol, o-isopropylphenol and 2, 6 di-t-butylphenol with DHAA, the yield of corresponding ester increased with the bulkyness of substituent at ortho-position of phenols.
2, 6-di-t- BuC6H4O (O) CR >o- iso- PrC6H4O (O) CR> o- MeC6H4O (O) CR
In the reaction of p-methyl, p-chloro and p-nitrophenols with DHAA, the yields of corresponding esters depended on the electron-donating ability of the substituent and showed the following order ;
p-MeC6H4O (O) CR>p-ClC6H4O (O) CR> p-NO2C6H4O (O) CR
The corresponding esters were obtained in higher yields in reaction of phenol, m-cresol, and 2, 6-di-t-butylphenol with DHAA compared to reaction of these phenols with homo DHAA.
