Nitric Acid → (4-Hydroxy-3-nitro-phenoxy)-acetonitrile

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].C(OCC)(=O)C>[N+](C)([O-])=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

Procedure

A solution of 7.5 g of (4-hydroxy-phenoxy)-acetonitrile dissolved in 60 ml of nitromethane was cooled in an ice bath and 3.88 ml of 70% nitric acid was added dropwise. After 45 minutes, the reaction mixture was poured into ethyl acetate, washed with brine, dried (MgSO4), and evaporated to dryness. The crude product was purified by silica gel chromatography eluting with ethyl acetate/hexane (1:3), giving 5.45 g of (4-hydroxy-3-nitro-phenoxy)-acetonitrile as a yellow solid, mp 113.1-114.1° C.