2-Tolyl isocyanate → 4-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl alcohol

Participants

Reaction Steps

15 g (81.8 mmol) of 3-methoxy-4-nitrobenzyl alcohol were hydrogenated in 500 mL of methyl tert-butyl ether over 1.3 g of palladium/carbon (10%; 50% water) while cooling in ice. After hydrogen uptake had ceased, the catalyst was filtered off, and 10.14 mL (81.8 mmol) of 2-methylphenyl isocyanate were added to the stirred filtrate over the course of 30 minutes. The reaction mixture was left to stand overnight, and the precipitated solid was filtered off with suction and washed with methyl tert-butyl ether. Yield: 20.5 g (88%).

Provenance & Evidence