Nitric Acid → 4-Cyclohexyl-2-nitrophenol

Reaction equation

CCOCC.[CH:6]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[N+:19]([O-])([OH:21])=[O:20]>O>[CH:6]1([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

Procedure

To a stirred mixture of 50 ml of water, 50 ml of ether and 10.0 g of 4-cyclohexylphenol, was added dropwise 12.6 ml of 60% nitric acid while cooling with ice. The temperature of the mixture was raised to room temperature and the reaction was carried out for a day. After 500 ml of water was added, the reaction mixture was extracted with 500 ml of ethyl acetate, washed with water and a brine successively and dried with anhydrous sodium sulfate. The drying agent was filtered off and the solvent was distilled away. The residue was purified by subjecting to silica-gel column-chromatography [eluent:chloroform] to give 6.92 g of 4-cyclohexyl-2-nitrophenol.