O-Xylene → HCID 13565674, compound

HRID 1262518Notes

Reaction equation

HRID 1262518 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.[OH-].[K+].Br[C:26]1[CH:32]=[C:31]([CH3:33])[C:29]([NH2:30])=[C:28]([CH3:34])[CH:27]=1>Cl[Cu].O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:26]2[CH:32]=[C:31]([CH3:33])[C:29]([NH2:30])=[C:28]([CH3:34])[CH:27]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 75634-BenzylphenolHCID 14797Potassium HydroxideHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 13565674HCID 13565674, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 64,4 g (0.35 mole) of p-benzylphenol, 500 ml of xylene and 28 g (0,45 mole) of pulverised potassium hydroxide is heated for 4 hours under reflux. The water formed is removed from the reaction mixture. Then 60 g (0,3 mole) of 4-bromo-2,6-dimethylaniline and 1 g of CuCl are added and the xylene is distilled off under nitrogen until the temperature in the reaction mixture is 160°-170°. The reaction mixture is stirred at this temperature for 12 hours, allowed to cool to 70°-80° C., and then taken up in 500 ml of toluene and filtered. The filtrate is diluted with diethyl ether, washed twice with 10% potassium hydroxide solution and three times with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue is purified over a column of silica gel with a 1:3 mixture of ethyl acetate/hexane as eluant. The eluant is evaporated off to give 4-(p-benzylphenoxy)-2,6-dimethylaniline as a dark liquid which after a time forms crystals with a melting point of 61°-63° C.

Workup

  1. temperatureis heated for 4 hours
  2. temperatureunder reflux
  3. customis removed from the reaction mixture
  4. distillationthe xylene is distilled off under nitrogen until the temperature in the reaction mixture
  5. customis 160°-170°
  6. temperatureto cool to 70°-80° C.
  7. filtrationfiltered
  8. additionThe filtrate is diluted with diethyl ether
  9. washwashed twice with 10% potassium hydroxide solution and three times with saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue is purified over a column of silica gel with a 1:3 mixture of ethyl acetate/hexane as eluant
  13. customThe eluant is evaporated off

Sources & evidence

ORD record
ord-f0b92d2b03ac44ccb891dd6807a2c3b6
Source dataset
uspto-grants-1984_06
Patent number
US04452795

Reaction notes

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