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 3 hrs. 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); NMR (200 MHz, CDCl3): 2.50(3H,s), 7.10(1H,d,J=8 Hz), 7.51(1H,dd,J=8 Hz), 7.95(1H,d,J=3 Hz).
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-527709443e6f4d37a1d5b9b8914c479d
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05219874
Reaction notes
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