2,6-Ditert-butyl-4-(4-nitrophenyl)phenol → 4-Hydroxy-4'-nitrobiphenyl

HRID 982154Notes

Reaction equation

HRID 982154 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14](C(C)(C)C)[C:13]([OH:20])=[C:12](C(C)(C)C)[CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1.[N+](C)([O-])=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 17349052,6-Ditert-butyl-4-(4-nitrophenyl)phenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1380784-Hydroxy-4'-nitrobiphenylYield 71.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6375NitromethaneSolvent

Procedure

To a solution of 5.0 g (15 mmol) of 4-(4'nitrophenyl)-2,6-di-tert-butylphenol in 50 mL of toluene was added a solution of 9.2 g (69 mmol) of aluminum chloride in 10 mL of nitromethane. This mixture was stirred at ambient temperature for 4 hours and poured into 100 mL of 1N HC1 mixed with ice. The resulting aqueous mixture was extracted with two 100-mL portions of ethyl acetate. Combination, drying (MgSO4), and concentration of the organic layers resulted in crystallization of 2.3 g (69% yield) of yellow 4-(4'-nitrophenyl)phenol, which may also be named as 4'-nitro-(1,1'-biphenyl)-4-ol: 1H NMR (DMSO-d6) 6.93 (d, 2H, J=9Hz), 7.64 (d, 2H, J=9Hz), 7.82 (d, 2H, J=9Hz), 8.25 (d, 2H, J=9Hz), 9.98 (broad s, 1H).

Workup

  1. additionpoured into 100 mL of 1N
  2. additionHC1 mixed with ice
  3. extractionThe resulting aqueous mixture was extracted with two 100-mL portions of ethyl acetate
  4. dry with materialCombination, drying (MgSO4), and concentration of the organic layers

Sources & evidence

ORD record
ord-ae961a65b75b4eee89de257b28ddb746
Source dataset
uspto-grants-1991_02
Patent number
US04994545

Reaction notes

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