Resorcinol → Phenol, 3-[(2-methylphenyl)amino]-

HRID 1833959Notes

Reaction equation

HRID 1833959 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.[NH2:9][C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.P(OCCCC)(OCCCC)OCCCC>O>[CH3:16][C:11]1[C:10]([NH:9][C:1]2[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=2)=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 7242O-ToluidineHCID 7623Tributyl phosphite

Product 1

HCID 80436Phenol, 3-[(2-methylphenyl)amino]-Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

250 parts of resorcinol, 300 parts of o-toluidine and 10 parts of tributyl phosphite are mixed. On heating to 120° C, a melt is formed. When the internal temperature has reached 190° C, the elimination of water commences. The internal temperature is raised to 230° C in the course of 5 hours. After this time, 41 parts of water have distilled off and the reaction has ended. Excess o-toluidine and resorcinol which may still be present are removed by applying reduced pressure, and the 3-hydroxy-2'-methyl-diphenylamine is then distilled, passing over at 185° C/3 mm Hg. 420 parts of end product of ND25 = 1.6455 are obtained, corresponding to a yield of 93% of theory.

Workup

  1. customa melt is formed
  2. customhas reached 190° C
  3. temperatureThe internal temperature is raised to 230° C in the course of 5 hours
  4. distillationAfter this time, 41 parts of water have distilled off
  5. customExcess o-toluidine and resorcinol which may still be present are removed
  6. distillationthe 3-hydroxy-2'-methyl-diphenylamine is then distilled
  7. custompassing over at 185° C/3 mm Hg
  8. custom420 parts of end product of ND25 = 1.6455 are obtained, corresponding to a yield of 93% of theory

Sources & evidence

ORD record
ord-329b8f3a59ad4a9ab327b19c914a8685
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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