5-[(2-Hydroxyethyl)amino]-o-cresol

75-21-8

2835-95-2

55302-96-0

In a 250 mL four-necked flask fitted with a thermometer and stirrer, 12.3 g (0.1 mol) of 5-amino-2-methylphenol was dissolved in 80 mL of diethylene glycol dimethyl ether and heated to 150 °C. Under slow stirring in a cold trap, 4.4 g (0.1 mol) of ethylene oxide was dissolved in 10 mL of diethylene glycol dimethyl ether and 0.3 g of NaY molecular sieve catalyst was added to a four-necked flask, followed by dropwise addition of the mixture. After the dropwise addition process lasted for 0.5 hr, the reaction was continued for 3 hr. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure, dried and the residue was cooled to give 16.6 g of 5-(2-hydroxyethyl)amino-o-cresol crude product. The crude product was dissolved in 100 mL of methanol-water mixed solvent and recrystallized to give 15.7 g of refined 5-(2-hydroxyethyl)amino-o-cresol in 94.1% yield and 99.52% purity.