Hydrochloric Acid → Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

HRID 620343Notes

Reaction equation

HRID 620343 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C1(C)C=CC=CC=1>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:1]([C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)([CH3:3])[CH3:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115Aniline2×HCID 584247p-Isopropenylphenol

Product 1

HCID 11148864Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 134.0 grams (1.0 mole) of p-isopropenylphenol and 186.0 grams (2.0 moles) of aniline was stirred and heated to 150° C. To the mixture was added 5.0 grams of a solution obtained by adding 1.28 grams of 10% hydrochloric acid to 93 grams of aniline and stirring the mixture well. The reaction was carried out for 3.0 hours (10,800 s) at the 150° C. reaction temperature. The reaction product was cooled to 120° C. then 350 milliliters of toluene was added. The product was then cooled to 25° C. and the solid precipitated product was recovered by filtration. The crude product was slurried into 350 milliliters of methanol and heated to a reflux then maintained for 15 minutes (900 s). After cooling, the product was recovered by filtration and dried under vacuum to yield 4-(1-(4-aminophenyl)-1-methylethyl)phenol as a white powder.

Workup

  1. customobtained
  2. stirringstirring the mixture well
  3. custom(10,800 s) at the 150° C. reaction temperature
  4. temperatureThe reaction product was cooled to 120° C.
  5. temperatureThe product was then cooled to 25° C.
  6. customthe solid precipitated product
  7. filtrationwas recovered by filtration
  8. temperatureheated to
  9. temperaturea reflux
  10. temperaturethen maintained for 15 minutes (900 s)
  11. temperatureAfter cooling
  12. filtrationthe product was recovered by filtration
  13. customdried under vacuum

Sources & evidence

ORD record
ord-53e4024461c343c4bb1dd5a73b54f312
Source dataset
uspto-grants-1989_04
Patent number
US04820798

Reaction notes

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