4-Methoxyphenol → 4-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

HRID 866019Notes

Reaction equation

HRID 866019 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=1[CH3:27]>CS(C)=O>[CH3:27][C:18]1[CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=[C:22]([CH3:23])[C:17]=1[O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of dimethylsulfoxide (875 ml), p-methoxyphenol (43.3g 0.3 48 mol), powdered potassium carbonate (69.9 g, 0.5 mol) and 4-chloro-3,5-dimethylnitrobenzene (see example 39, 64.6 g; 0.348 mol) is heated at a temperature of 125° for 18 hours. The suspension is cooled to 25° and pumped onto ice water (2620 ml) with stirring. The mixture is stirred for 2 hours, the product is filtered, washed with water (4×300 ml) and air dried. A solution of the product in tert-butylmethyl ether (3 L) is dried over magnesium sulfate and treated with charcoal (6.4 g) for 2.5 hours. The drying agent is filtered off and the filtrate concentrated in vacuo at 50°/3 mm Hg to give product which is recrystallized from toluene (212 ml) and petroleum ether (600 ml) to give 3,5-dimethyl-4-(4'-methoxyphenoxy)nitrobenzene, m.p. 120°-123°.

Workup

  1. temperatureis heated at a temperature of 125° for 18 hours
  2. temperatureThe suspension is cooled to 25°
  3. stirringThe mixture is stirred for 2 hours
  4. filtrationthe product is filtered
  5. washwashed with water (4×300 ml) and air
  6. customdried
  7. dry with materialA solution of the product in tert-butylmethyl ether (3 L) is dried over magnesium sulfate
  8. additiontreated with charcoal (6.4 g) for 2.5 hours
  9. filtrationThe drying agent is filtered off
  10. concentrationthe filtrate concentrated in vacuo at 50°/3 mm Hg
  11. customto give product which
  12. customis recrystallized from toluene (212 ml) and petroleum ether (600 ml)

Sources & evidence

ORD record
ord-df7d1f3b597240d9821cb8675370c6eb
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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