Potassium Carbonate → Benzene, 5-methoxy-1,3-dimethyl-2-nitro-

HRID 1284962Notes

Reaction equation

HRID 1284962 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[CH3:13]C1C=CC(S(C)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(O)C>[CH3:11][C:6]1[CH:5]=[C:4]([O:12][CH3:13])[CH:3]=[C:2]([CH3:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18521p-Tolyl methyl sulfoneHCID 1384663,5-Dimethyl-4-nitrophenol

Product 1

HCID 143760Benzene, 5-methoxy-1,3-dimethyl-2-nitro-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

3,5-dimethyl-4-nitrophenol (33.43 g), methyl p-toluene sulfonate (40.97 g) and K2CO3 (31.79 g) are stirred at reflux in 200 ml of acetone for four and one half hours and then stirred at R.T. overnight. The reaction mixture is filtered to give a dark amber filtrate. The filtrate is concentrated in vacuo to a yellowish brown solid which is dissolved in ethyl acetate washed with saturated aqueous sodium chloride, dried and concentrated in vacuo. The concentrate is distilled (87°-104° C./0.10 mm) to give a yellow waxy looking solid. The solid is dissolved in hot ethanol and recrystallized, M.P. 50°-52° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto give a dark amber filtrate
  3. concentrationThe filtrate is concentrated in vacuo to a yellowish brown solid which
  4. dissolutionis dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. distillationThe concentrate is distilled (87°-104° C./0.10 mm)
  9. customto give a yellow waxy
  10. customrecrystallized

Sources & evidence

ORD record
ord-9624c1617f7c405aab115ce95d47a3cb
Source dataset
uspto-grants-1986_01
Patent number
US04564640

Reaction notes

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