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

HRID 1977647Notes

Reaction equation

HRID 1977647 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>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CCCCCC>[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

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 79483,5-DimethylphenolHCID 24268Sodium Nitrate

Product 1

HCID 1384663,5-Dimethyl-4-nitrophenolYield 36.8%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8058HexaneSolvent

Procedure

The bi-phasic mixture of 3,5-dimethylphenol (25 g, 0.20 mol) and sodium nitrate (17.4 g, 0.20 mol) in a 1:1 mixture of ether-water (800 ml) containing 40 ml of concentrated HCl was vigorously stirred for several hours. n-Bu4NHSO4 (3.4 g, 0.01 mol) and additional conc. HCl (40 ml) were added and stirring continued for 60 hrs. The reaction mixture was extracted with ether (×2). The combined ether extracts were washed with 1.0N HCl, brine and dried over anhydrous Na2SO4. Concentration in vacuo followed by flash chromatography (hexane-EtOAc: 99:1 to 40:60) on silica gel gave, after trituration with hexane, 12.3 g of the title compound of this step as a yellow solid.

Workup

  1. stirringstirring
  2. extractionThe reaction mixture was extracted with ether (×2)
  3. washThe combined ether extracts were washed with 1.0N HCl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationConcentration in vacuo
  6. customgave

Sources & evidence

ORD record
ord-47375191d921406088d2a2fbe16f8cea
Source dataset
uspto-grants-2001_05
Patent number
US06235740B1

Reaction notes

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