Dichloromethane → 2-Tert-butyl-5-(4-tert-butylphenyl)phenol

HRID 1079

Reaction equation

HRID 1079 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:18](Cl)([CH3:21])([CH3:20])[CH3:19].CCC[CH2:26][CH2:27][CH3:28].[CH2:29](Cl)Cl>>[C:18]([C:14]1[CH:15]=[CH:16][C:11]([C:5]2[CH:6]=[CH:7][C:8]([C:27]([CH3:26])([CH3:28])[CH3:29])=[CH:9][CH:10]=2)=[CH:12][C:13]=1[OH:17])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 10486tert-BUTYL CHLORIDEHCID 113813-PhenylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 99257712-Tert-butyl-5-(4-tert-butylphenyl)phenol

Procedure

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.

Workup

  1. additionis added dropwise
  2. customThe organic phase is separated
  3. extractionthe aqueous remainder is twice extracted with 50 mL portions of methylene chloride
  4. washThe combined organic solutions are washed twice with 50 mL portions of water, 50 mL of saturated aqueous sodium chloride solution
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customUpon standing at room temperature
  8. custom3-hydroxy-4-t-butylbiphenyl crystallizes from the solution
  9. customThis is isolated by filtration
  10. customsuccessively recrystallized from 100 mL portions of pentane until its melting point
  11. customThe material is obtained as a white crystalline compound in 6.8 g
  12. customyield

Sources & evidence

ORD record
ord-f19bba0b067b4f289e036aa25822eeb2
Source dataset
uspto-grants-1998_03
Patent number
US05723500

Linked notes

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