Sulfuric Acid → 4-Ethynyl-1,2-dinitrobenzene

HRID 1415460Notes

Reaction equation

HRID 1415460 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:9]=[C:10](Cl)C=O)([O-:5])=[O:4].S(=O)(=O)(O)O>O1CCOCC1>[N+:3]([C:6]1[CH:7]=[C:8]([C:9]#[CH:10])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 544649072-Chloro-3-(3,4-dinitrophenyl)prop-2-enal

Product 1

HCID 214824734-Ethynyl-1,2-dinitrobenzeneYield 40.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 50 ml of a rapidly stirred 0.5 m sodium hydroxide solution maintained at 60° C was rapidly added a solution containing 4.0 g (15.5 mmoles) of 3,4-dinitro-α-chlorocinnamaldehyde dissolved in 10 ml of dioxane. The mixture was stirred for 5 minutes, at which time the solution was cooled and neutralized with 1N sulfuric acid. The reaction mixture was extracted into methylene chloride, and the combined extracts washed with several portions of water. The methylene chloride solution was reduced in volume to 25 ml and filtered through a 1 × 3 inch dry column of silica gel, eluting with methylene chloride. Evaporation of the eluate yielded 1.2 g (40% yield) of 3,4-dinitroethynyl benzene as a light brown oil.

Workup

  1. additionwas rapidly added a solution
  2. temperaturewas cooled
  3. extractionThe reaction mixture was extracted into methylene chloride
  4. washthe combined extracts washed with several portions of water
  5. filtrationfiltered through a 1 × 3 inch
  6. customdry column of silica gel
  7. washeluting with methylene chloride
  8. customEvaporation of the

Sources & evidence

ORD record
ord-bce49efc29204cf28efe51be58e9853a
Source dataset
uspto-grants-1977_01
Patent number
US04005144

Reaction notes

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