4-Nitrobenzaldehyde → HCID 237433, compound

HRID 2413675Notes

Reaction equation

HRID 2413675 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH:21]=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 1118Sulfuric AcidHCID 74764'-MethoxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 237433HCID 237433, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

30 g of p-nitrobenzaldehyde was reacted with 30 g of p-methoxyacetophenone in 200 ml of acetic acid in the presence of 34 ml of sulfuric acid at room temperature for 1 day, and the reaction mixture was poured into 1 liter of ice-water. After neutralizing the mixture with 48 g of NaOH, cyrstals formed were collected by filtration, and recrystallized from acetoneacetonitrile (0.2 liter/1.3 liter) to obtain 37.6 g of the desired compound. m.p. 171°-173° C.

Workup

  1. customformed
  2. filtrationwere collected by filtration
  3. customrecrystallized from acetoneacetonitrile (0.2 liter/1.3 liter)

Sources & evidence

ORD record
ord-5d99a182d4b64fb0a6485e50060216f1
Source dataset
uspto-grants-1988_01
Patent number
US04719174

Reaction notes

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