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

HRID 1861892Notes

Reaction equation

HRID 1861892 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-butylpyridine

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-yt-butylpyridine (Compound B3, 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-39ea67f4e32a420e8c762cdc4d893f51
Source dataset
uspto-grants-2003_03
Patent number
US06534544B1

Reaction notes

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