反応 #1175

反応方程式

hexane

aluminum chloride

3-phenylphenol

t-butylchloride

methylene chloride

→

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

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise
2. 2
   その他The organic phase is separated
3. 3
   抽出the aqueous remainder is twice extracted with 50 mL portions of methylene chloride
4. 4
   洗浄The combined organic solutions are washed twice with 50 mL portions of water, 50 mL of saturated aqueous sodium chloride solution
5. 5
   ろ過filtered
6. 6
   その他evaporated in vacuo
7. 7
   その他Upon standing at room temperature
8. 8
   その他3-hydroxy-4-t-butylbiphenyl crystallizes from the solution
9. 9
   その他This is isolated by filtration
10. 10
    その他successively recrystallized from 100 mL portions of pentane until its melting point
11. 11
    その他The material is obtained as a white crystalline compound in 6.8 g
12. 12
    その他yield

実験手順

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.

出典