Réaction #302866

ord-9624ea7e963d448e9d21772267560ddb

Équation de réaction

CC(C)(C)c1ccccc1O
t-butylphenol
Nc1ccccc1
aniline
CC(C)(C)c1ccccc1
t-BuPh

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONmixed in an oil bath at 90° C
  2. 2
    Autreafter about 30 minutes
  3. 3
    Autrethe reaction was quenched
  4. 4
    TempératureThe cooled crude product
  5. 5
    Lavagewas base-washed twice through a solvent extraction
  6. 6
    Lavagewashed once with deionized water
  7. 7
    LavageAfter washing
  8. 8
    Séchagethe organic layer was dried with MgSO4
  9. 9
    Filtrationfiltered
  10. 10
    AutreThe residual solution was dried
  11. 11
    Autrea rotary evaporator
  12. 12
    Autreto remove the solvent
  13. 13
    Autrethe purified product was dried in a vacuum oven at 40° C. for 6 hours

Mode opératoire

15 g (0.1 mol) of t-butylphenol, 6.31 g (0.21 mol) of p-formaldehyde and 10.24 g (0.11 mol) of aniline were added to a 100 ml one-neck round-bottom flask and mixed in an oil bath at 90° C. When the initially opaque mixture became a dark brown transparent gel type material after about 30 minutes, the reaction was quenched using tetrahydrofuran (THF), and then the mixture was cooled to room temperature. The cooled crude product was base-washed twice through a solvent extraction using a 1N NaOH aqueous solution, and washed once with deionized water. After washing, the organic layer was dried with MgSO4 and filtered. The residual solution was dried using a rotary evaporator to remove the solvent, and the purified product was dried in a vacuum oven at 40° C. for 6 hours to obtain t-BuPh-a.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08192892B2uspto-grants-2012_06