I1-+ I11-P IV+ V-+ acyclic products. The formation of 4-methyl-6-nitrosoguaiacol (11) as the first intermediate was inferred from the fact that the first detectable reaction of I with nitric acid was nitration via nitrosonium (NO+) ion. When compound I was heated with dilute nitric acid, and the reaction was quenched at an early stage, 4-methyl-6-nitroguaiaco17~* was isolated in crystalline form. The product pattern and nitric acid consumption found upon further ...