Water → 6-Methyl-3-pyridinecarboxaldehyde

HRID 868340Notes

Reaction equation

HRID 868340 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.O>N1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[CH3:9][C:6]1[N:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 962WaterHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 101925666-Methyl-3-pyridinecarboxaldehydeYield 42.7%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent2×

Procedure

Chromium trioxide (11.5 g) is slowly added to 170 ml of pyridine at 20° C., and 10 g of the crude 5-hydroxymethyl-2-methylpyridine in 70 ml of pyridine is added in one portion to the complex. The temperature is raised to reflux temperature for 2 hours, and the mixture is refluxed for 1.5 hours. After cooling, 250 ml of water is added, and the mixture is extracted with five 150-ml portions of diethyl ether. The combined extracts are dried over magnesium sulfate and concentrated to give 4.2 g of crude 6-methyl-3-pyridinecarbaldehyde.

Workup

  1. temperatureThe temperature is raised
  2. temperatureto reflux temperature for 2 hours
  3. temperaturethe mixture is refluxed for 1.5 hours
  4. temperatureAfter cooling
  5. extractionthe mixture is extracted with five 150-ml portions of diethyl ether
  6. dry with materialThe combined extracts are dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6de38bcfe4674abb8e542cb0c74a5e9d
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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