Acetone → 2,6-Di-tert-butylisonicotinic acid

HRID 2304780Notes

Reaction equation

HRID 2304780 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:6]=[C:5]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1.CC(C)=[O:19]>>[C:13]([C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([C:9]([CH3:10])([CH3:12])[CH3:11])[N:6]=1)[C:2]([OH:19])=[O:1])([CH3:16])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 180AcetoneHCID 129668344-Hydroxymethyl-2,6-di-t-butylpyridine2×

Product 1

HCID 47369412,6-Di-tert-butylisonicotinic acid

Procedure

Jone's reagent was added dropwise to a solution of 4-hydroxymethyl-2,6-di-t-butylpyridine (Compound B, 302 mg, 1.37 mmol) in 5 ml of acetone until the solution changed color from light yellow to orange (55 drops of Jone's reagent were consumed). After 5 minutes 2 ml of isopropanol were added to the reaction mixture, and a green precipitate of Cr3+ salt was formed. The precipitate was removed by filtration and the solution was diluted with ethyl acetate, then washed with brine, water and dried over MgSO4. After filtration, the solvent was removed to give the desired product as a white solid (227 mg). 1H NMR δ 7.71 (s, 2H), 1.34 (s, 18H).

Workup

  1. customyellow to orange (55 drops of Jone's reagent were consumed)
  2. additionAfter 5 minutes 2 ml of isopropanol were added to the reaction mixture
  3. customa green precipitate of Cr3+ salt was formed
  4. customThe precipitate was removed by filtration
  5. additionthe solution was diluted with ethyl acetate
  6. washwashed with brine, water
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-ef91e27c79494580b244137c03c3772e
Source dataset
uspto-grants-2002_08
Patent number
US06437129B1

Reaction notes

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