Sulfuric Acid → 4-(3-Ethynylphenoxy)-1,2-dinitrobenzene

HRID 1283510Notes

Reaction equation

HRID 1283510 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[CH:13]=[C:14](Cl)C=O)([O-:5])=[O:4].S(=O)(=O)(O)O>O1CCOCC1>[C:13]([C:12]1[CH:11]=[C:10]([CH:20]=[CH:19][CH:18]=1)[O:9][C:8]1[CH:21]=[CH:22][C:23]([N+:24]([O-:26])=[O:25])=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)#[CH:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 537336452-Chloro-3-[3-(3,4-dinitrophenoxy)phenyl]prop-2-enal

Product 1

HCID 203569524-(3-Ethynylphenoxy)-1,2-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 50 ml of refluxing 1N sodium hydroxide solution, under a nitrogen atmosphere, was added a solution containing 10 g (0.028 mole) of m-(3,4-dinitrophenoxy)-α-chlorocinnamaldehyde dissolved in 50 ml of 1,4-dioxane. The dark mixture was refluxed for one-half hour at which time the solution was cooled and acidified with 10% sulfuric acid. The reaction mixture was extracted with several 50 ml portions of ether, and the combined extracts evaporated to dryness. The residue was chromatographed on a 1 × 12 inch dry column of silica gel. Elution of the column using 3/1 hexane/methylene chloride produced a first band of sideproduct. Further elution using 1/1 hexane/methylene chloride yielded a second band which contained the desired product. Evaporation of the eluate to dryness in vacuo afforded 2 g (25%) of 4-(3-ethynylphenoxy)-o-dinitrobenzene as light yellow crystals, m.p. 68°-69°C.

Workup

  1. additionunder a nitrogen atmosphere, was added a solution
  2. temperatureThe dark mixture was refluxed for one-half hour at which time the solution
  3. temperaturewas cooled
  4. extractionThe reaction mixture was extracted with several 50 ml portions of ether
  5. customthe combined extracts evaporated to dryness
  6. customThe residue was chromatographed on a 1 × 12 inch
  7. customdry column of silica gel
  8. washElution of the column
  9. customproduced a first band of sideproduct
  10. washFurther elution
  11. customyielded a second band which

Sources & evidence

ORD record
ord-f2b379d8737a422e8a47cf34bc731c05
Source dataset
uspto-grants-1976_08
Patent number
US03975444

Reaction notes

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