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

HRID 2291014Notes

Reaction equation

HRID 2291014 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]>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

4

Reactant 2

HCID 867Malonic AcidHCID 74493-Nitrobenzaldehyde

Product 1

HCID 683902-Propenoic acid, 3-(3-nitrophenyl)-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 151 g of m-nitrobenzaldehyde, 200 g of pyridine, and 120 g of malonic acid was heated for 3 hours with stirring. The mixture was poured into ice water. The resulting crystalline deposit was collected by filtration, washed with water, and dried, yielding 180 g of m-nitrocinnamic acid having a melting point of 156° C.

Workup

  1. temperaturewas heated for 3 hours
  2. filtrationThe resulting crystalline deposit was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f97f08053d5442b689bdb5c6cfc3f4df
Source dataset
uspto-grants-1986_10
Patent number
US04619888

Reaction notes

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