Toluene → HCID 67403176, compound

HRID 1186414Notes

Reaction equation

HRID 1186414 reaction equation
[I-].[CH2:2]([O:4][CH:5]([O:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][N+:9]([CH3:12])=[CH:8][CH:7]=1)[CH3:3].[OH-:16].[K+].C1(C)C=CC=CC=1>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:12][N:9]1[CH:8]=[CH:7][C:6]([CH:5]([O:4][CH2:2][CH3:3])[O:13][CH2:14][CH3:15])=[CH:11][C:10]1=[O:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 67400684HCID 67400684, compound

Product 1

HCID 67403176HCID 67403176, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

4-(Diethoxymethyl)-1-methylpyridinium iodide (3.43 g, 10.6 mmol) was dissolved in water (70 mL). To this, a solution of potassium ferricyanide (38.4 g, 117 mmol) in water (85 mL) was added dropwise under a nitrogen atmosphere at 0° C. over 1 hour. To this, an aqueous solution (16 mL) of potassium hydroxide (9.40 g, 167 mmol) was added dropwise at the same temperature over 30 minutes. To this, toluene (100 mL) was added and the mixture was stirred at 40° C. for 30 minutes. Then, extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 1-methyl-4-(diethoxymethyl)-2(1H)-pyridone (1.20 g, yield: 53%).

Workup

  1. extractionThen, extraction with dichloromethane
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-07e69d89a6014c2aaf3fe04d1ab7bc01
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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