3-Nitrobenzaldehyde → 2-Propenoic acid, 2-methyl-3-(3-nitrophenyl)-

HRID 848500Notes

Reaction equation

HRID 848500 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:16]C(=O)CC)(=[O:15])[CH2:13][CH3:14].C([O-])(=O)CC.[Na+].[OH-].[NH4+]>>[CH3:14][C:13](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:12]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 14923Ammonium HydroxideHCID 31263Propionic anhydrideHCID 2723816Sodium Propionate

Product 1

HCID 41802852-Propenoic acid, 2-methyl-3-(3-nitrophenyl)-

Procedure

A mixture of 75 g. of 3-nitrobenzaldehyde, 98 g. of propionic anhydride and 48 g. of sodium propionate was heated at 170° to 175° C. for 1.25 hours, and then it was cooled and poured into 750 ml. of ice-water. Concentrated ammonium hydroxide was then added until a basic pH was obtained. The mixture was warmed on a steam bath for a few minutes and then the small amount of insoluble material was removed by filtration. The filtrate was acidified with concentrated hydrochloric acid and the solid was recovered by filtration. This crude product was recrystallized from aqueous ethanol to give 81 g. of the title compound, m.p. 200.5°-202° C.

Workup

  1. additionA mixture of 75 g
  2. temperatureit was cooled
  3. additionpoured into 750 ml
  4. customwas obtained
  5. temperatureThe mixture was warmed on a steam bath for a few minutes
  6. customthe small amount of insoluble material was removed by filtration
  7. filtrationthe solid was recovered by filtration
  8. customThis crude product was recrystallized from aqueous ethanol
  9. customto give 81 g

Sources & evidence

ORD record
ord-d299654f24434de58436a63e5b5a2068
Source dataset
uspto-grants-1981_10
Patent number
US04296120

Reaction notes

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