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

HRID 2256501Notes

Reaction equation

HRID 2256501 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 (2620ml) 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 (3L) is dried over magnesium sulfate and treated with charcoal (6.4g) for 2.5 hours. The drying agent is filtered off and the filtrate concentrated in vacuo at 50°/3mm Hg to give product which is recrystallized from toluene (212ml) 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 (3L) is dried over magnesium sulfate
  8. additiontreated with charcoal (6.4g) for 2.5 hours
  9. filtrationThe drying agent is filtered off
  10. concentrationthe filtrate concentrated in vacuo at 50°/3mm Hg
  11. customto give product which
  12. customis recrystallized from toluene (212ml) and petroleum ether (600 ml)

Sources & evidence

ORD record
ord-48e351bb2a1d4f3fafe7dc9c48c70ff5
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

Loading…