Water → 1-(4-Carboxyphenyl)-2-nitropropene

HRID 2412649Notes

Reaction equation

HRID 2412649 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].O.[N+:13]([CH2:16][CH3:17])([O-:15])=[O:14]>C(N)CCC>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:16]([N+:13]([O-:15])=[O:14])[CH3:17])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6587NitroethaneHCID 120884-Formylbenzoic acid

Product 1

HCID 542582771-(4-Carboxyphenyl)-2-nitropropene

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 4-carboxybenzaldehyde (38.44 g) in nitroethane (360 ml) and butylamine (2 ml) was heated at reflux for 2 hours with azeotropic distillation of water using a Dean and Stark apparatus The solution was cooled to room temperature and the resulting solid was collected and recrystallised from isopropanol (250 ml) with hot filtration to give 1-(4-carboxyphenyl)-2-nitropropene (31.57 g) in the form of a yellow crystalline solid, m.p. 212°-214° C.

Workup

  1. customthe resulting solid was collected
  2. customrecrystallised from isopropanol (250 ml) with hot filtration

Sources & evidence

ORD record
ord-6bf80c77bce34c21ac74e007d2c591f0
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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