Phenol → 2,6-Bis(1-methylethyl)-4-phenoxybenzenamine

HRID 2165246Notes

Reaction equation

HRID 2165246 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH:10]([C:13]1[CH:19]=[C:18](Br)[CH:17]=[C:16]([CH:21]([CH3:23])[CH3:22])[C:14]=1[NH2:15])([CH3:12])[CH3:11]>C1(C)C(C)=CC=CC=1.[Cu](Cl)Cl>[CH:10]([C:13]1[CH:19]=[C:18]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=[C:16]([CH:21]([CH3:23])[CH3:22])[C:14]=1[NH2:15])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 117801144-Bromo-2,6-diisopropylaniline

Product 1

HCID 132721392,6-Bis(1-methylethyl)-4-phenoxybenzenamine

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 7237O-XyleneSolvent

Procedure

48.9 g of phenol are dissolved in 500 ml of xylene, and to this solution are added 30.2 g of pulverised potassium hydroxide in an atmosphere of nitrogen. The reaction mixture is stirred and heated to boiling point, while continuously distilling off the water that is formed. After addition of 0.6 g of copper chloride and 100 g of 2,6-diisopropyl-4-bromoaniline, the mixture is stirred for 8 hours at 150°-155° C., then cooled, and filtered with suction. The filtrate is washed with 15% sodium hydroxide solution (150 ml) and with two 150 ml portions of water. The organic phase is separated and dried over sodium sulfate. The solvent is removed by distillation and the product is distilled, affording the compound of the formula ##STR5## with a boiling point of 103°-104° C./0.01 torr and a melting point of 71°-72° C. (after recrystallisation from hexane).

Workup

  1. temperatureheated
  2. distillationwhile continuously distilling off the water that
  3. customis formed
  4. stirringthe mixture is stirred for 8 hours at 150°-155° C.
  5. temperaturecooled
  6. filtrationfiltered with suction
  7. washThe filtrate is washed with 15% sodium hydroxide solution (150 ml) and with two 150 ml portions of water
  8. customThe organic phase is separated
  9. dry with materialdried over sodium sulfate
  10. customThe solvent is removed by distillation
  11. distillationthe product is distilled
  12. customaffording the compound of the formula ##STR5## with a boiling point of 103°-104° C./0.01 torr
  13. customa melting point of 71°-72° C. (after recrystallisation from hexane)

Sources & evidence

ORD record
ord-544fb30b095e4c3a808c333333e4d5d0
Source dataset
uspto-grants-1990_07
Patent number
US04939257

Reaction notes

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