Cyanoacetic acid → (E,E)-2-Carboxy-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

HRID 392481Notes

Reaction equation

HRID 392481 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH:6]=[CH:7][CH:8]=O.[C:16]([CH2:18][C:19]([OH:21])=[O:20])#[N:17]>>[C:19](/[C:18](=[CH:8]/[CH:7]=[CH:6]/[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([OH:13])=[C:11]([O:14][CH3:15])[CH:10]=1)/[C:16]#[N:17])([OH:21])=[O:20]

Participants

3

Reactant 2

HCID 9740Cyanoacetic acidHCID 1192162-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-

Product 1

HCID 9965375(E,E)-2-Carboxy-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

Procedure

The compound was prepared as described in Example 3 by adding 3,5-dimethoxy-4-hydroxycinnamaldehyde (0.15 g, 0.72 mmol) to cyanoacetic acid (0.061 g, 0.72 mmol). After refluxing for 1 h and recrystallization from ethanol a yellow solid was obtained (0.15 g, 75%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 1 h
  3. customrecrystallization from ethanol a yellow solid
  4. customwas obtained (0.15 g, 75%)
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-78ad4023914a4c638fdec8547058e4e6
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

Loading…