1,2-Dimethyl-3-nitrobenzene → 3-Methyl-5-nitrobenzaldehyde

HRID 979822Notes

Reaction equation

HRID 979822 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1C)([O-:3])=[O:2].BrN1[C:17](=[O:18])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:10][C:6]1[CH:7]=[C:8]([CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 67391,2-Dimethyl-3-nitrobenzeneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 137539983-Methyl-5-nitrobenzaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of nitroxylene (150 g), N-bromo succinimide (160 g) and benzoylperoxide (4.8 g) in carbontetrachloride (1200 ml) was heated to reflux for 4 hours with a mechanical stirrer. The precipitated succinimide was filtered and the filtrate evaporated. The oily residue was dissolved in chloroform (800 ml) and bistetrabutyl ammonium chromate (420 g) was added. The solution was refluxed for 3 hours, cooled to room temperature and diluted with benzene (500 ml) and filtered. The salts were washed with ethyl acetate until no desired material appeared on thin layer chromatography. The combined organic layer was evaporated and the residue, after chromatography, afforded the desired aldehyde in 50% yield. m.p. 81°-82° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours with a mechanical stirrer
  3. filtrationThe precipitated succinimide was filtered
  4. customthe filtrate evaporated
  5. dissolutionThe oily residue was dissolved in chloroform (800 ml)
  6. additionbistetrabutyl ammonium chromate (420 g) was added
  7. temperatureThe solution was refluxed for 3 hours
  8. additiondiluted with benzene (500 ml)
  9. filtrationfiltered
  10. washThe salts were washed with ethyl acetate until no desired material
  11. customThe combined organic layer was evaporated

Sources & evidence

ORD record
ord-486ea25158584a33a37c3d21dad1a6cb
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

Loading…