Methanol → 6-(Difluoromethyl)-4-ethyl-2-(trifluoromethyl)-3,5-pyridinedicarboxylic acid

HRID 1111078Notes

Reaction equation

HRID 1111078 reaction equation
[F:1][CH:2]([F:25])[C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([CH2:14][CH3:15])[C:6]([C:16]([O:18]CC)=[O:17])=[C:5]([C:21]([F:24])([F:23])[F:22])[N:4]=1.CO.[OH-].[K+]>O>[F:25][CH:2]([F:1])[C:3]1[N:4]=[C:5]([C:21]([F:24])([F:22])[F:23])[C:6]([C:16]([OH:18])=[O:17])=[C:7]([CH2:14][CH3:15])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium Hydroxide2×HCID 13957657Diethyl 2-(difluoromethyl)-4-ethyl-6-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 139576946-(Difluoromethyl)-4-ethyl-2-(trifluoromethyl)-3,5-pyridinedicarboxylic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1-liter flask is charged with 60 g (0.163 mole) of the product of Example 12 and 200 ml of methyl alcohol. In another flask, 150 ml of water and 21.52 g (0.326 mole) of potassium hydroxide are combined. The aqueous KOH is poured into the 1-liter flask and the mixture is heated to reflux overnight. The reaction mixture is cooled and extracted once with ethyl ether. The aqueous layer is acidified with concentrated hydrochloric acid and extracted with ethyl ether. The organics are dried on anhydrous magnesium sulfate, filtered, and concentrated to yield 26.72 g (52%) of the desired product, m.p. 237°-239° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted once with ethyl ether
  5. extractionextracted with ethyl ether
  6. dry with materialThe organics are dried on anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-40837933743644c8bbbd60a7e3a56219
Source dataset
uspto-grants-1990_12
Patent number
US04978384

Reaction notes

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