Nitric Acid → 4-(Methylsulfanyl)-2-nitrophenol
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[N+:10]([O-])([OH:12])=[O:11]>C(Cl)Cl>[N+:10]([C:7]1[CH:8]=[C:3]([S:2][CH3:1])[CH:4]=[CH:5][C:6]=1[OH:9])([O-:12])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(methylthio)phenol(5.0 g) in methylene chloride (100 mls) was added 30% nitric acid absorbed on silica (9.29 g) and the mixture stirred at room temperature for 3hrs. The mixture was filtered and washed with methylene chloride. The solvent was evaporated and the residue was purified by flash chromatography eluting with ethyl acetate and hexane (15:85 v/v ) to give 2-nitro-4-(methylthio)phenol as an orange solid (2.22 g);
Workup
- customabsorbed on silica (9.29 g)
- filtrationThe mixture was filtered
- washwashed with methylene chloride
- customThe solvent was evaporated
- customthe residue was purified by flash chromatography
- washeluting with ethyl acetate and hexane (15:85 v/v )
Sources & evidence
- ORD record
- ord-81bed632dbd54875956ae110e783d8c1
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05410064
Reaction notes
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