4-tert-Butylphenol → 1-Tert-butyl-4-propoxybenzene

HRID 2058849Notes

Reaction equation

HRID 2058849 reaction equation
[Na].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH2:13](Cl)[CH2:14][CH3:15]>C(O)C>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 108991-ChloropropaneHCID 5360545Sodium

Product 1

HCID 50880031-Tert-butyl-4-propoxybenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 70 ml. of ethanol (absolute), 0.92 g. of sodium metal was dissolved and 6.0 g. (0.04 M) of 4-tert-butylphenol was added and then, 3.5 g. (0.044 M) of n-propylchloride was added. The mixture was refluxed for 20 hours and ethanol was distilled off and water was added. The reaction product was extracted with benzene and benzene layer was washed with 3% NaOH aqueous solution and with water and dehydrated over sodium sulfate and then, benzene was distilled off and a residue was distilled under a reduced pressure to obtain 4-tert-butyl-1-n-propoxybenzene. The product was dissolved into 6 ml. of glacial acetic acid and then, 12 ml. of fuming nitric acid (d=1.5) was added at 0° to 5° C. to react them for 1 hour and then, the reaction was continued at the ambient temperature for 1 hour at 35° to 40° C. for 4 hours. The reaction mixture was poured into ice water and the product was extracted with chloroform and washed with water, with 3% Na2CO3 aqueous solution and with water and dehydrated over sodium sulfate and chloroform was distilled off and the residue was recrystallized from ethanol to obtain 4.5 g. (43%) of a pale yellow crystal. (melting point of 106° to 107° C.)

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. distillationethanol was distilled off
  3. additionwater was added
  4. extractionThe reaction product was extracted with benzene and benzene layer
  5. washwas washed with 3% NaOH aqueous solution and with water
  6. distillationbenzene was distilled off
  7. distillationa residue was distilled under a reduced pressure

Sources & evidence

ORD record
ord-79564bdbe8604619bfa849d8bc64f61b
Source dataset
uspto-grants-1982_03
Patent number
US04319919

Reaction notes

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