Sulfuric Acid → HCID 10018077, compound

HRID 1607679Notes

Reaction equation

HRID 1607679 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[C:6]([N+:25]([O-:27])=[O:26])=[CH:7][C:8]([CH3:24])=[C:9]([CH:23]=1)[C:10]([CH:12](C(OCC)=O)C(OCC)=O)=[O:11].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C.O>[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[C:6]([N+:25]([O-:27])=[O:26])=[CH:7][C:8]([CH3:24])=[C:9]([C:10](=[O:11])[CH3:12])[CH:23]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 53848590HCID 53848590, compound

Product 1

HCID 10018077HCID 10018077, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of diethyl 5-(2,4-difluorophenoxy)-2-methyl-4-nitrobenzoylmalonate (2.1 g) and sulfuric acid (1 ml) in acetic acid (6 ml) and water (5 ml) was refluxed for hours. The reaction mixture was neutralized with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The oily residue was purified by column chromatography on silica gel (25 g) eluting with a mixture of toluene and ethyl acetate (10:1) to give crystals of 5'-(2,4-difluorophenoxy)-2'-methyl-4'-nitroacetophenone (0.69 g).

Workup

  1. temperaturewas refluxed for hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe oily residue was purified by column chromatography on silica gel (25 g)
  7. washeluting with a mixture of toluene and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-5b42f16793ce40a1909cad03cda487e4
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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