Hydrochloric Acid → 3,5-Dimethyl-4-nitrophenol

HRID 2299246Notes

Reaction equation

HRID 2299246 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N+:10]([O-])([O-:12])=[O:11].[Na+].Cl.C(OCC)(=O)C>O.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[C:7]=1[N+:10]([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79483,5-DimethylphenolHCID 8857Ethyl AcetateHCID 24268Sodium Nitrate

Product 1

HCID 1384663,5-Dimethyl-4-nitrophenolYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, 3,5-dimethylphenol (40.9 mmoles) was dissolved in 40 mL water and 40 mL ether. To this was added 1.5 equivalents (61.4 mmoles) of sodium nitrate (NaNO3). The reaction was cooled in an ice bath and 50 mL concentrated HCl was slowly added to the reaction. The reaction was warmed to room temperature and followed by TLC (ethyl acetate:hexanes, 1:1) until the reaction was complete (0.5 hour). The reaction was extracted into ether (×3), washed with saturated NaHCO3, saturated NaCl, dried over MgSO4, filtered, rinsed with ether, and concentrated. The product was purified using silica-gel chromatography, yielding 3,5-dimethyl-4-nitro-phenol as a yellow solid (2.05 grams; 30% yield). The product was characterized by NMR (DMSO).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. custom(0.5 hour)
  3. extractionThe reaction was extracted into ether (×3)
  4. washwashed with saturated NaHCO3, saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. washrinsed with ether
  8. concentrationconcentrated
  9. customThe product was purified

Sources & evidence

ORD record
ord-f02ce99026024830b05f7ab2dcfee078
Source dataset
uspto-grants-2002_12
Patent number
US06495681B1

Reaction notes

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