Nitric Acid → (2,6-Dimethyl-3-nitrophenyl)methanol

Fuming nitric acid (0.52 ml) was added dropwise to a solution of 2,6-dimethylbenzyl acetate (1.78 g) in acetic anhydride (8.9 ml) at 0° C. and then stirred for 2.5 hours. After being stirred for an additional 30 minutes at room temperature, the mixture was poured onto crushed ice, neutralized with sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with water and evaporated in vacuo. To the residue were added methanol (24 ml) and 1N sodium hydroxide solution (12 ml) and the mixture was stirred at room temperature for 1 hour and evaporated in vacuo. The residue was washed with water, air-dried, and recrystallized from a mixture of benzene and n-hexane to give 2,6-dimethyl-3-nitrobenzyl alcohol (1.26 g).

1. stirringAfter being stirred for an additional 30 minutes at room temperature
2. additionthe mixture was poured
3. customonto crushed ice
4. extractionextracted with ethyl acetate
5. washThe extract was washed with water
6. customevaporated in vacuo
7. additionTo the residue were added methanol (24 ml) and 1N sodium hydroxide solution (12 ml)
8. stirringthe mixture was stirred at room temperature for 1 hour
9. customevaporated in vacuo
10. washThe residue was washed with water
11. customair-dried
12. customrecrystallized from a mixture of benzene and n-hexane

ORD record

ord-47ea6cec6ae94c0691307689ff30bb02

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04782055