Acetic Acid → HCID 12276122, compound

HRID 428145

Reaction equation

HRID 428145 reaction equation
[CH3:1][S-:2].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12].C(O)(=O)C>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([S:2][CH3:1])[CH2:10][N+:11]([O-:13])=[O:12])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7096881,2-Dimethoxy-4-(2-nitrovinyl)benzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 12276122HCID 12276122, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methanethiolate (0.62 g, 8.8 mmol) in methanol (20 ml), trans-3,4-dimethoxy-β-nitrostyrene (1.42 g, 8 mmol) was added and stirred at room temperature for 5 minutes. Further, acetic acid (0.46 ml) was added and stirred for 5 minutes. After evaporating methanol to a half amount under reduced pressure, water was added and extracted with dichloromethane and the organic layers were combined, washed with water and dried over sodium sulfate. The solvent was distilled out under reduced pressure and the residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to yield 2-(3,4-dimethoxyphenyl)-2-(methylthio)nitroethane (1.24 g, 60%).

Workup

  1. stirringstirred for 5 minutes
  2. customAfter evaporating methanol to a half amount under reduced pressure, water
  3. additionwas added
  4. extractionextracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled out under reduced pressure
  8. customthe residue was isolated
  9. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0fe0dd5283cf4905b42ee79271a7a6cb
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Linked notes

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