2-Methyl-2-butene → 4-(Pyridin-4-yl)benzoic acid

HRID 1359598Notes

Reaction equation

HRID 1359598 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.CC(=CC)C.[O-:20]Cl=O.[Na+]>C(O)(C)(C)C.O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]([OH:20])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 6396734-(4-Pyridyl)benzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 15208114-(Pyridin-4-yl)benzoic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a suspension of 4-[pyridin-4-yl]-benzaldehyde (approx. 2.8 g, 15 mmol) (reference example 8a) in t-butanol (100 mL) was added 2-methy-but-2-ene (15 mL) followed by a solution comprised of NaClO2 (14.7 g, tech. grade) and NaH2PO4.H2O (14.7 g, 105 mmol) in H2O (100 mL). This mixture was stirred for 20 min then the precipitated solid filtered off. This solid was washed with water then set aside. The organic phase of the mother liquor was separated then washed with brine, dried over MgSO4 and concentrated to give a solid. This material was combined with the solid obtained by filtration and dried under vacuum to give 2.34 g of the title compound. 1H NMR (DMSO) d 7.77 (d, J=6 Hz, 2H), 7.93 (d, J=8 Hz, 2H), 8.06 (d, J=8 Hz, 2H), 8.70 (d, J=6 Hz, 2H). MS (EI) m/z 199 (M)+.

Workup

  1. filtrationthe precipitated solid filtered off
  2. washThis solid was washed with water
  3. customThe organic phase of the mother liquor was separated
  4. washthen washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a solid
  8. customobtained by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-3c7ee8d0a9284991bb756d965371865f
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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