2-Methyl-4-nitrophenol → HCID 67106647, compound

HRID 1910793Notes

Reaction equation

HRID 1910793 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH2:19][CH2:20][CH2:21]I>C(#N)C>[Cl:18][CH2:19][CH2:20][CH2:21][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropane

Product 1

HCID 67106647HCID 67106647, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-methyl-4-nitrophenol (1.0 g, 6.5 mmol) and potassium carbonate (1.8 g, 13.0 mmol) in acetonitrile was added 1-chloro-3-iodopropane (1.2 g, 5.9 mmol). The mixture was heated at reflux overnight then cooled to r.t. and filtered, the solids being further washed with acetonitrile. The combined filtrates were evaporated to dryness. The crude residue was dissolved in ethyl acetate and washed successively with saturated sodium bicarbonate solution, water and brine solution. The organic phase was dried over sodium sulfate, filtered and concentrated to afford 1-(3-chloro-propoxy)-2-methyl-4-nitro-benzene (700 mg, 52%) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. washthe solids being further washed with acetonitrile
  5. customThe combined filtrates were evaporated to dryness
  6. dissolutionThe crude residue was dissolved in ethyl acetate
  7. washwashed successively with saturated sodium bicarbonate solution, water and brine solution
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d400f2b33dff499f83256f56f2ca60c0
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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