Nitromethane → HCID 50853072, compound

HRID 1297493Notes

Reaction equation

HRID 1297493 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:4].[N+:13]([CH3:16])([O-:15])=[O:14]>CO>[CH2:3]([C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:16]/[N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 208614-Ethylbenzaldehyde

Product 1

HCID 50853072HCID 50853072, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

An aq. 6M NaOH solution (1.05 eq) was added to a methonolic solution of 4-ethylbenzaldehyde (1 eq) and nitromethane (1 eq) stirred at 0° C. During the slow addition of base, maintain the temperature between 10-15° C. The reaction generates a thick white precipitate. To allow smooth stirring, an additional amount of MeOH was added. After stirring for an additional 15 min., the ice bath was removed. Upon reaching RT, water was added to the reaction, which subsequently turned clear. The clear solution was added to a flask containing a stirred 6M aq. HCl solution. A yellow crystalline precipitate formed. After 10 min., the crystalline product was filtered, washed thoroughly with water, suction dried and recrystallized from abs. EtOH. 4-ethyl trans-beta-nitrostyrene (2) was afforded as a yellow crystalline product in 52% yield and >99% purity (LC/MS m/z 178.2 MH.

Workup

  1. additionDuring the slow addition of base
  2. temperaturemaintain the temperature between 10-15° C
  3. stirringAfter stirring for an additional 15 min.
  4. customthe ice bath was removed
  5. customUpon reaching RT
  6. additionwater was added to the reaction, which subsequently turned clear
  7. additionThe clear solution was added to a flask
  8. additioncontaining a stirred 6M aq. HCl solution
  9. customA yellow crystalline precipitate formed
  10. filtrationthe crystalline product was filtered
  11. washwashed thoroughly with water, suction
  12. customdried
  13. customrecrystallized from abs

Sources & evidence

ORD record
ord-ea453a953fe34d65b1bd439072280c69
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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