A New Synthesis of 2-t-Butyl-5-methylanisole

Abstract

2-t-Butyl-5-methylanisole (TBMMA) is an intermediate for Musk ambrette, one of the artificial musks.Methylation of m-eresol with methanol at 150 v1800C, and t-butylation of m-methylanisole with t-butanol or isobutanol at 70yv120eC were studied, The reaetion vessel used was a flowing stream system on a stationary catalyst bede As a catalyst, the strongly acidic eation exchange resin of macroreticular type was used.It was found that t-butyl group was selectively introdu6ed in the positien ortho to the methoxy greup and para to the methyl group. The result is consistent with those of Carpenter, The yield in t-butyiation with t-butanol was 66 mol%, and selectivity was 80 mol%at 90 C (Fig.2, 3). With isobutanol, the yield was 45 mgl%e, and selectivity was 90 mol%at 1000C (Fig.4, 5).