Acetate → 1-(2,3,4-TRIMETHOXYPHENYL)-2-NITROPROPENE

HRID 1154609Notes

Reaction equation

HRID 1154609 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[N+:15]([CH2:18][CH3:19])([O-:17])=[O:16].C([O-])(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[C:18]([N+:15]([O-:17])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 175AcetateHCID 6587NitroethaneHCID 750062,3,4-Trimethoxybenzaldehyde

Product 1

HCID 6200721-(2,3,4-TRIMETHOXYPHENYL)-2-NITROPROPENEYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.9 g of 2,3,4-trimethoxybenzaldehyde, 3.7 g of nitroethane, 2.5 g of Amberlite IR-45 acetate and 200 ml of toluene is refluxed for 20 hours while removing the resultant water. After the reaction is completed, the reaction mixture is filtered, and the filtrate is evaporated to remove solvent. The residue thus obtained is recrystallized from a mixture of isopropyl ether and hexane. 4.3 g of 1-(2,3,4-trimethoxyphenyl)-2-nitropropene are thereby obtained as yellow cubes. M.p. 57°-58° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. customwhile removing the resultant water
  3. filtrationthe reaction mixture is filtered
  4. customthe filtrate is evaporated
  5. customto remove solvent
  6. customThe residue thus obtained
  7. customis recrystallized from a mixture of isopropyl ether and hexane

Sources & evidence

ORD record
ord-875f3b0722264028a5c1a7c1dd44c11e
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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