Methyl p-toluenesulfonate → 1-Methoxy-2,4-dimethyl-3-nitrobenzene

HRID 1154008Notes

Reaction equation

HRID 1154008 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][C:3]=1[OH:12].[CH3:13]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 133699642,4-Dimethyl-3-nitrophenol

Product 1

HCID 133699671-Methoxy-2,4-dimethyl-3-nitrobenzeneYield 88.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 32.12 grams of 2,4-dimethyl-3-nitrophenol, 35.78 grams of methyltosylate and 28.5 grams of anhydrous K2CO3 in 200 ml of acetone is heated to reflux for 12 hours. The reaction mixture is filtered leaving a tan solid. The filtrate is concentrated in vacuo. The concentrated filtrate is taken up in ethyl acetate and extracted with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride. The remaining ethyl acetate layer is dried, filtered and concentrated in vacuo to give a dark oil which is distilled (T=80°-87° C./50μ) to give 30.95 grams of a yellow solid which is recrystallized from absolute ethanol, M.P. 53°-55° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 12 hours
  3. filtrationThe reaction mixture is filtered
  4. customleaving a tan solid
  5. concentrationThe filtrate is concentrated in vacuo
  6. extractionextracted with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride
  7. dry with materialThe remaining ethyl acetate layer is dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a dark oil which
  11. distillationis distilled (T=80°-87° C./50μ)

Sources & evidence

ORD record
ord-dc43643a014b44e292c760688ea54eaa
Source dataset
uspto-grants-1984_12
Patent number
US04487779

Reaction notes

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