Nitric Acid → 4-Hexyl-2-nitrophenol

HRID 1108919Notes

Reaction equation

HRID 1108919 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+:14]([O-])([OH:16])=[O:15].O>C1C=CC=CC=1.C(O)(=O)C>[N+:14]([C:11]1[CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=[CH:9][C:10]=1[OH:13])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962Water2×HCID 171324-n-Hexylphenol

Product 1

HCID 190211464-Hexyl-2-nitrophenolYield 92.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

1.00 g (5.61 mM) of 4-hexylphenol was dissolved in a mixture solvent of 2.0 ml of benzene and 1.3 ml of acetic acid. To the solution, 0.62 ml (8.15 mM) of nitric acid (60%, density=1.38) was gradually added dropwise under cooling with iced water and stirring below 8° C. After the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and subjected to reduced-pressure distillation into a solid. The solid was purified by silica gel column chromatography (eluent: toluene/hexane=1/2) to obtain 1.16 g of oily yellow 2-nitro-4-hexylphenol (Yield: 92.6%).

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationsubjected to reduced-pressure distillation into a solid
  5. customThe solid was purified by silica gel column chromatography (eluent: toluene/hexane=1/2)

Sources & evidence

ORD record
ord-7021c8ba587847f9bd0b9f9b8cd246f1
Source dataset
uspto-grants-1994_06
Patent number
US05318720

Reaction notes

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