Methyl Isobutyl Ketone → 2-Isopropyl-4-nitrophenol

HRID 502628Notes

Reaction equation

HRID 502628 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][C:4](=[O:6])[CH3:5].O.[N+:9]([CH:12]([CH:15]=O)[CH:13]=O)([O-:11])=[O:10].[Na].[OH-].[Na+]>C(O)C.O>[CH:2]([C:3]1[CH:15]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=[CH:5][C:4]=1[OH:6])([CH3:7])[CH3:1]

Participants

6

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 14798Sodium HydroxideHCID 71317419Sodium nitromalonaldehyde hydrate

Product 1

HCID 5289542-Isopropyl-4-nitrophenolYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Methyl-2-pentanone (4.85 g, 48 mmol) in 40 mL of ethanol was added dropwise to a solution of sodium nitromalonaldehyde monohydrate (7.61 g, 48 mmol) in 40 mL of water. NaOH (48 ml of 1N aqueous solution) was then added to the reaction mixture. The mixture was stirred at room temperature overnight, and solvent was removed under reduced pressure. The residue was diluted with water and neutralized, then extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography with silica eluting with 15% ethyl acetate in hexanes to yield 4.7 g of 2-isopropyl-4-nitrophenol.

Workup

  1. customsolvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionneutralized, then extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography with silica eluting with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4e7713e699974148b743aef39dfc210a
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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