Hydrochloric Acid → 2-Propenoic acid, 3-(3-nitrophenyl)-

HRID 2166010Notes

Reaction equation

HRID 2166010 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(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1.Cl>O.N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH:13][C:14]([OH:16])=[O:15])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 74493-NitrobenzaldehydeHCID 8082Piperidine

Product 1

HCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

30 g. 3-Nitrobenzaldehyde and 30 g. malonic acid were heated in 60 ml. pyridine at a maximum temperature of 50° C. until a clear solution was obtained. Subsequently, 3 ml. piperidine were added thereto and the solution was heated for 1 hour at 80° C. Thereafter, it was heated under reflux for 3 hours. The solution was then poured into 400 ml. water which contained 50 ml. concentrated hydrochloric acid. The precipitated solid material was filtered off and washed with water. It was subsequently dissolved in 400 ml. water in which 8 g. sodium hydroxide had been dissolved. Insoluble materials were then filtered off and the 3-nitrocinnamic acid obtained was again precipitated out by acidification with hydrochloric acid. The compound was recrystallised from ethanol, the yield being 17 g.; m.p. 204° C.

Workup

  1. temperatureThereafter, it was heated
  2. temperatureunder reflux for 3 hours
  3. additionThe solution was then poured into 400 ml
  4. filtrationThe precipitated solid material was filtered off
  5. washwashed with water
  6. dissolutionIt was subsequently dissolved in 400 ml
  7. dissolutionsodium hydroxide had been dissolved
  8. filtrationInsoluble materials were then filtered off

Sources & evidence

ORD record
ord-40c9d1747f58411e9476876e68882be1
Source dataset
uspto-grants-1990_07
Patent number
US04943526

Reaction notes

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