Réaction #1175

Équation de réaction

hexane

aluminum chloride

3-phenylphenol

t-butylchloride

methylene chloride

→

2-tert-butyl-5-(4'-tert-butylphenyl) phenol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added dropwise
2. 2
   AutreThe organic phase is separated
3. 3
   Extractionthe aqueous remainder is twice extracted with 50 mL portions of methylene chloride
4. 4
   LavageThe combined organic solutions are washed twice with 50 mL portions of water, 50 mL of saturated aqueous sodium chloride solution
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated in vacuo
7. 7
   AutreUpon standing at room temperature
8. 8
   Autre3-hydroxy-4-t-butylbiphenyl crystallizes from the solution
9. 9
   AutreThis is isolated by filtration
10. 10
    Autresuccessively recrystallized from 100 mL portions of pentane until its melting point
11. 11
    AutreThe material is obtained as a white crystalline compound in 6.8 g
12. 12
    Autreyield

Mode opératoire

A suspension of 0.8 aluminum chloride in 50 mL of anhydrous methylene choloride is stirred under an anhydrous nitrogen atmosphere at 5°-15° C. while a solution of 17 g of 3-phenylphenol and 24 mL of t-butylchloride in 50 mL of anhydrous methylene chloride is added dropwise. The resultant mixture is stirred for 2 hours, then allowed to stand at room temperature for 12 hours. The reaction mixture is poured over 150 g of ice/water and shaken. The organic phase is separated and the aqueous remainder is twice extracted with 50 mL portions of methylene chloride. The combined organic solutions are washed twice with 50 mL portions of water, 50 mL of saturated aqueous sodium chloride solution, rendered anhydrous over sodium sulfate, filtered, and evaporated in vacuo. The residue is taken into about 150 mL of hexane. Upon standing at room temperature, 3-hydroxy-4-t-butylbiphenyl crystallizes from the solution. This is isolated by filtration and successively recrystallized from 100 mL portions of pentane until its melting point becomes constant. The material is obtained as a white crystalline compound in 6.8 g yield, m.p. 86°-87° C. The original hexane filtrates also produce another crop of crystals which provides 1.1 g of 2-tert-butyl-5-(4'-tert-butylphenyl) phenol, m.p. 143°-145° C. after several recrystalizations from pentane. An additional 1.12 g of this material are obtained from the chromatography of the mother liquor residues.

Source