1-Nitropropane → Benzene, 1-fluoro-2-(2-nitro-1-buten-1-yl)-

HRID 1648224Notes

Reaction equation

HRID 1648224 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:10]([CH2:13][CH2:14][CH3:15])([O-:12])=[O:11].C([O-])(=O)C.[NH4+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:13]([N+:10]([O-:12])=[O:11])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 79031-NitropropaneHCID 67970o-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 517165Ammonium Acetate

Product 1

HCID 4226107Benzene, 1-fluoro-2-(2-nitro-1-buten-1-yl)-Yield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

30 ml of acetic acid were added to 4.73 g (38.11 mmole) of 2-fluorobenzaldehyde, 4.41 g (49.49 mmole) of nitropropane and 3.23 g (41.90 mmole) of ammonium acetate, and the resulting mixture was heated under reflux, whilst stirring, for 4 hours. At the end of this time, the reaction mixture was cooled to room temperature, neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and then xylene was added to the solution. The mixture was concentrated by evaporation under reduced pressure, to give 7.4 g of the title compound as a pale yellow oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. extractionextracted with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. additionxylene was added to the solution
  6. concentrationThe mixture was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8a20029a5bb544398c0a525a16f71cec
Source dataset
uspto-grants-1995_07
Patent number
US05436242

Reaction notes

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