Some Derivatives of Creosol

Reactivity in Cleavage of Dimethoxybenzenes by Sodium in Liquid Ammonia

“…2-Methoxy-4-methylphenol was prepared from vanillin according to Martin's modified Clemmensen reduction: 43,44 yield 44%; bp 70-77 °C/ 4-5 Torr (lit. 44 105-106 °C/15 Torr); after redistillation, >99% pure by GC analysis; bp 68-74 °C/4.5 Torr; 1 H NMR (60 MHz, CCl4) δ 2.2 (s, 3H), 3.5 (m, 3H), 5.5 (broad s, 1H), 6.3 (m, 3H); MS m/z 138 (M + ). 4-Methoxy-3-methylphenol was prepared from o-cresol by a method identical to that described above for 4-methoxy-2-methylphenol.…”

“…2-Methoxy-5-methylphenol was prepared via diazotization of 2-methoxy-5-methylaniline and ensuing hydroxydediazoniation; orange plates; >99% pure by GC analysis; yield 16.3%; 1 H NMR (60 MHz, CCl 4 ) δ 2.2 (s, 3H), 3.7 (s, 3H), 5.2 (broad s, 1H), 6.4 (m, 3H); MS m / z 138 (M + ). 2-Methoxy-4-methylphenol was prepared from vanillin according to Martin's modified Clemmensen reduction: , yield 44%; bp 70−77 °C/4−5 Torr (lit . 105−106 °C/15 Torr); after redistillation, >99% pure by GC analysis; bp 68−74 °C/4.5 Torr; 1 H NMR (60 MHz, CCl 4 ) δ 2.2 (s, 3H), 3.5 (m, 3H), 5.5 (broad s, 1H), 6.3 (m, 3H); MS m / z 138 (M + ).…”

Expectorants, Antitussives, and Related Agents

“…The compounds are usually classed as direct-acting or stimulant expectorants, but their mechanisms of action have not been well studied. Cresol is obtained by the Clemmensen reduction of vanillin (3), whereas guaiacol can be prepared by a number of methods including the mercuric oxide oxidation of lignin (qv) (4), the zinc chloride reduction of acetovanillone (5), and the diazotization and hydrolysis of o-anisidine (6).…”