2-Nitrophenol → 2-(2-Methylthioethoxy)nitrobenzene

HRID 743133Notes

Reaction equation

HRID 743133 reaction equation
[CH3:1][S:2][CH2:3][CH2:4]Cl.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([O-:8])=[O:7].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][S:2][CH2:3][CH2:4][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium Carbonate

Product 1

HCID 539101632-(2-Methylthioethoxy)nitrobenzeneYield 63.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-methylthioethylchloride (18.0 g, 0.16 mole), o-nitrophenol (20.8 g, 0.15 mole) and potassium carbonate (24.7 g, 0.18 mole) was refluxed in acetonitrile for 24 h. The reaction mixture was filtered and the solvent was evaporated. The residue was dissolved in methylene chloride and washed with water once and thereafter twice with a saturated sodium carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated giving 20.2 g (63%) of the title compound as an oily residue.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with water once
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8701becf66044f1c8d3a6fcd0dc67ce6
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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