Hydrochloric Acid → 2-Methyl-5-(2-nitrovinyl)furan

HRID 1511605Notes

Reaction equation

HRID 1511605 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[N+:12]([CH3:15])([O-:14])=[O:13]>>[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:15][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 120975-MethylfurfuralHCID 14798Sodium Hydroxide

Product 1

HCID 5380062-Methyl-5-(2-nitrovinyl)furanYield 57.5%

Procedure

5-Methyl-2-furaldehyde (2.75 g) was gradually added by dropping, with stirring under ice cooling, to a solution prepared by dropping 3.05 g of nitromethane into 50 mL of an ice-cooled 20% aqueous solution of sodium hydroxide. After completion of the addition, the mixture was vigorously stirred for 10 minutes more to finish the reaction and the reaction solution was slowly poured over 60 mL of an ice-cooled 6N hydrochloric acid. The mixed solution was stirred for 10 minutes and the resulting separated crystals were filtered, washed with water and dried to give 2.20 g of the objective compound as yellow powder.

Workup

  1. customprepared
  2. additionAfter completion of the addition
  3. stirringthe mixture was vigorously stirred for 10 minutes more
  4. customthe reaction
  5. stirringThe mixed solution was stirred for 10 minutes
  6. customthe resulting separated crystals
  7. filtrationwere filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-10d876ecc96c405189bd848a5faf1d3d
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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