4-Chloro-2-nitrobenzaldehyde → HCID 12595973, compound

HRID 597137Notes

Reaction equation

HRID 597137 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]>C(O)C>[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][C:13]([Cl:15])=[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 12595973HCID 12595973, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a solution of 1.1 g. of sodium methylate in 32 ml. of ethanol, 6.2 g. of diethyl 2-nitro-4-chlorobenzyl phosphonate was dissolved. A solution of 3.7 g. of 2-nitro-4-chlorobenzaldehyde in 32 ml. of ethanol was dropwise added to said solution with stirring at ambient temperature. After the solution was stirred for 1 hour, the yellow crystalline materials formed were filtered and washed with a small amount of ethanol to give 5 g. (74% yield) of trans-2,2'-dinitro-4,4'-dichlorostilbene. Its recrystallization from glacial acetic acid gave a product having a melting point of 247° to 248° C.

Workup

  1. stirringAfter the solution was stirred for 1 hour
  2. customthe yellow crystalline materials formed
  3. filtrationwere filtered
  4. washwashed with a small amount of ethanol
  5. customto give 5 g

Sources & evidence

ORD record
ord-8ba822f37cbd427d9771e0467735e0ce
Source dataset
uspto-grants-1977_03
Patent number
US04013639

Reaction notes

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