Nitric Acid → 4-Hexyl-2-nitrophenol

Participants

Reaction Steps

1.00 g (5.61 mM) of 4-hexylphenol was dissolved in a mixture solvent of 2.0 ml of benzene and 1.3 ml of acetic acid. To the solution, 0.62 ml (8.15 mM) of nitric acid (60%, density=1.38) was gradually added dropwise under cooling with iced water and stirring below 8° C. After the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and subjected to reduced-pressure distillation into a solid. The solid was purified by silica gel column chromatography (eluent: toluene/hexane=1/2) to obtain 1.16 g of oily yellow 2-nitro-4-hexylphenol (Yield: 92.6%).

Provenance & Evidence