Nitric Acid → 4-(Methylsulfanyl)-2-nitrophenol

HRID 1587805Notes

Reaction equation

HRID 1587805 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

HCID 944Nitric AcidHCID 140864-(Methylthio)phenol

Product 1

HCID 187958574-(Methylsulfanyl)-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customabsorbed on silica (9.29 g)
  2. filtrationThe mixture was filtered
  3. washwashed with methylene chloride
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography
  6. 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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