2,6-Di-tert-butylphenol → 2,6-Di-tert-butyl-4-nitrophenol

HRID 1707837Notes

Reaction equation

HRID 1707837 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.[O:21]=[N+:22]=[O:23]>C(Cl)Cl.S1(CCCC1)(=O)=O>[C:11]([C:7]1[CH:8]=[C:9]([N+:22]([O-:23])=[O:21])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 314052,6-Di-tert-butylphenolHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 697652,6-Di-tert-butyl-4-nitrophenol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 31347SulfolaneSolvent

Conditions

Temperature
-60 °C

Procedure

Dissolve 2,6-di-t-butylphenol (721 mg, 3.5 mmol) in methylene chloride (10 mL) and cool to -60° C. Add, by dropwise addition, a solution of nitronium tetrafluoroborate (25 mL of a 0.5M solution in sulfolane, 12.5 mmol) in methylene chloride (15 mL). Warm slowly to 10° C. and partition between methylene chloride (75 mL) and water (75 mL). Separate the aqueous phase and extract with methylene chloride (50 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify and separate by flash silica gel chromatography to give the title compound.

Workup

  1. additionAdd, by dropwise addition
  2. temperatureWarm slowly to 10° C.
  3. custompartition between methylene chloride (75 mL) and water (75 mL)
  4. customSeparate the aqueous phase
  5. extractionextract with methylene chloride (50 mL)
  6. dry with materialCombine the organic phases, dry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. customPurify
  9. customseparate by flash silica gel chromatography

Sources & evidence

ORD record
ord-4dd4177f0f8f41bea282bcc6e5fe4d2c
Source dataset
uspto-grants-1994_10
Patent number
US05354782

Reaction notes

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