p-Toluidine → P-Anisidine

Participants

Reaction Steps

Column chromatography was performed in the dark, using 50% EtOAc/50% hexanes as eluent. Three bands emerged; the first band was a fluorescent impurity, the second and third bands were the di-(rf˜0.7) and monomethyl aniline (rf˜0.65), respectively. Rotary evaporation of the middle fractions gave the product in modest yield (˜1 gram, 16% based on starting p-anisidine). The off-white solid was further purified by sublimation (high vacuum, heated at 30° C., collected on a small cold finger). Product isolated at this stage was sufficiently pure for reductive quenching purposes. Due to its short shelf-life (stored at 4° C., under argon, protected from light), the compound was frequently recrystallized from warm water before use. 1H NMR (CDCl3): δ 3.30 (s, N—CH3, 6H), 3.88 (s, O—CH3, 3H), 7.58 (d, 21), 7.15 (d, 21). GC-MS calcd for C9H13NO (M−H+) m/z 150, found 150.

Provenance & Evidence