4-Methyl-2-nitrobenzaldehyde → trans-2,2'-Dinitro-4-methylstilbene

HRID 597136Notes

Reaction equation

HRID 597136 reaction equation
C[O-].[Na+].[N+:4]([C:7]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:8]=1[CH:9]=O)([O-:6])=[O:5]>C(O)C>[N+:4]([C:7]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:8]=1/[CH:9]=[CH:9]/[C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[N+:4]([O-:6])=[O:5])([O-:6])=[O:5]

Participants

4

Reactant 2

HCID 5904464-Methyl-2-nitrobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 21446813trans-2,2'-Dinitro-4-methylstilbeneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1.4 g. of sodium methylate in 40 ml. of ethanol was added 6.8 g. of diethyl ortho-nitrobenzyl phosphonate. While stirring the solution at ambient temperature, a solution of 4.1 g. of 2-nitro-4-methylbenzaldehyde in 40 ml. of ethanol was dropwise added. After being stirred for 1.5 hours and allowed to stand overnight, the yellow crystals formed were filtered and washed with a small amount of ethanol to give 6.0 g. (85% yield) of trans-2,2'-dinitro-4-methylstilbene. This compound was then recrystallized from benzene to give a product melting at 170° to 171° C.

Workup

  1. stirringAfter being stirred for 1.5 hours
  2. customthe yellow crystals formed
  3. filtrationwere filtered
  4. washwashed with a small amount of ethanol
  5. customto give 6.0 g

Sources & evidence

ORD record
ord-1d3c4aa9c5744f5a9c0238d4240efff0
Source dataset
uspto-grants-1977_03
Patent number
US04013639

Reaction notes

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