4-Chloro-2-nitrobenzaldehyde → HCID 21446807, compound

HRID 597134Notes

Reaction equation

HRID 597134 reaction equation
C[O-].[Na+].[N+:4]([C:7]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:8]=1[CH:9]=O)([O-:6])=[O:5]>CO>[N+:4]([C:7]1[CH:14]=[C:13]([Cl: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 796744-Chloro-2-nitrobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 21446807HCID 21446807, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a solution of 1.6 g. of sodium methylate in 20 ml. of methanol, 8.2 g. of diethyl ortho-nitrobenzyl phosphonate was dissolved. To this solution was dropwise added a solution of 5.5 g. of 2-nitro-4-chlorobenzaldehyde in 20 ml. of methanol with stirring at ambient temperature. After stirring continuously for one hour, crystalline materials formed which were filtered and washed with a small amount of ethanol and water to give 8.2 g. (90% yield) of trans-2,2'-dinitro-4-chlorostilbene. Recrystallization of this compound from ethyl acetate gave a product having a melting point of 158.5° to 159° C.

Workup

  1. additionTo this solution was dropwise added a solution of 5.5 g
  2. customcrystalline materials formed which
  3. filtrationwere filtered
  4. washwashed with a small amount of ethanol and water
  5. customto give 8.2 g

Sources & evidence

ORD record
ord-389d883699424fc8ac77c981f2c24b28
Source dataset
uspto-grants-1977_03
Patent number
US04013639

Reaction notes

Loading…