Reaction #1973959

Reaction equation

water

Methyl 3,5-di-tert-butyl-2-hydroxybenzoate

nitric acid

→

title compound

Yield 89.0%

methyl 3-tert-butyl-2-hydroxy-5-nitrobenzoate

Yield 89.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONWhen the addition
2. 2
   workup.WAITto stand 30 min
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Washwashed with water
5. 5
   Otherdried

Procedure

Methyl 3,5-di-tert-butyl-2-hydroxybenzoate (28.66 g, 108.4 mmol) was dissolved with stirring in 430 mL glacial acetic acid and the resulting mixture was treated drop wise with fuming nitric acid (90%, 179.26 mL). When the addition was complete, the resulting mixture was stirred for 2.5 h. The reaction mixture was poured into a 2.0 L of crushed ice and allowed to stand 30 min. Afterwards, 1.0 L of water was added and the ice water mixture was allowed to melt. The mixture was then filtered, washed with water and dried to provide the title compound (24.57 g, 89%).

Source