Nitric Acid → Phenol, 5-(1,1-dimethylethyl)-2-nitro-

HRID 1913685Notes

Reaction equation

HRID 1913685 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[C:7]([OH:11])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 11450Phenol, 3-(1,1-dimethylethyl)-

Product 1

HCID 11958960Phenol, 5-(1,1-dimethylethyl)-2-nitro-Yield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 5 g of 3-tert-butylphenol and 30 ml of acetic acid, a mixture of 3.0 g of 70% nitric acid and 10 ml of acetic acid was added dropwise with the temperature kept at 10-15° C. and stirred for two hours. The reaction mixture was poured into ice water and extracted with ethyl acetate twice. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.82 g of 5-tert-butyl-2-nitrophenol.

Workup

  1. additionwas added dropwise with the temperature
  2. customkept at 10-15° C.
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-357680ddca8144f2a4d0dbd194643cbb
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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