Potassium Hydroxide → 4,6-Diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylic acid

HRID 64567Notes

Reaction equation

HRID 64567 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:6]=1[C:19]([O:21]CC)=[O:20])([CH3:3])[CH3:2].[OH-].[K+]>CO>[CH:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:6]=1[C:19]([OH:21])=[O:20])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13726788Ethyl 4,6-diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

Product 1

HCID 137267904,6-Diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.5 g (0.0283 mol) of product of Example 6, 10 g of KOH and 150 ml of methanol was held at reflux for 16 hours. Methanol was removed under reduced pressure. The residue was treated with 300 ml of water and extracted with ether. The aqueous layer was poured into 50 ml of concentrated HCl and extracted with ether. The ether extract was concentrated. The residual solid (7.7 g) was recrystallized from hexane-ether to give 6.4 g (73.6%) of acid product: mp 147°-150° C.

Workup

  1. temperatureat reflux for 16 hours
  2. customMethanol was removed under reduced pressure
  3. additionThe residue was treated with 300 ml of water
  4. extractionextracted with ether
  5. additionThe aqueous layer was poured into 50 ml of concentrated HCl
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. concentrationwas concentrated
  9. customThe residual solid (7.7 g) was recrystallized from hexane-ether

Sources & evidence

ORD record
ord-0ea1e0e4a739450eb588d343f04c6701
Source dataset
uspto-grants-1986_09
Patent number
US04609399

Reaction notes

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