2,5-Dimethylanisole → 4-Methylcatechol

Temperature

2.5 °C

To an ice-cold concentrated nitric acid (200 mL) was added slowly under stirring over a period of 20 minutes 2-methoxy-1,4-dimethylbenzene (25 g, 184 mmol). To this cold reaction mixture, sodium nitrite (38 g, 552 mmol) was added slowly in lots over a period of 1 h while maintaining the temperature below 2° C. The reaction mixture was stirred at between 0-5° C. for 5 h. The reaction mass was poured into ice-cold water (1000 mL), and the precipitated solid was filtered, washed with cold water (100 mL) and dried. The crude solid was crystallized from ethanol and water (7:1) to yield compound 1 (15 g, 45%).

1. additionwas added slowly in lots over a period of 1 h
2. temperaturewhile maintaining the temperature below 2° C
3. filtrationthe precipitated solid was filtered
4. washwashed with cold water (100 mL)
5. customdried
6. customThe crude solid was crystallized from ethanol and water (7:1)

ORD record

ord-7a72b8535733418f8997d35b7dd91617

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434724B2