Methanol → HCID 178524830, compound

HRID 542104Notes

Reaction equation

HRID 542104 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([OH:14])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[OH-].[Na+].CO>C(OCC)(=O)C.Cl>[OH:14][C:7]1[CH:6]=[C:5]([C:15]([F:16])([F:17])[F:18])[N:4]=[C:3]([C:2]([F:20])([F:1])[F:19])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178470034HCID 178470034, compound2×

Product 1

HCID 178524830HCID 178524830, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2,6-bis(trifluoromethyl)-4-hydroxy-3-pyridinecarboxylate (product of Example 3, 15 g, 0.0495 mol) in 5% aqueous sodium hydroxide (60 ml, 0.148 mol) was refluxed for 3 hours. The reaction was complete as judged by TLC (10% methanol in ethyl acetate). The mixture was then poured into a mixture of ice in concentrated aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, and concentrated to give a light brown solid (13 g). It was treated with petroleum ether to give 11.9 g of a white solid (83%); mp 168°-172° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8770f4f2ab3e49adae28c8ac52de8525
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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