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

HRID 1264207Notes

Reaction equation

HRID 1264207 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 12a) in t-butanol (100 mL) is 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 is stirred for 20 minutes then the precipitated solid filtered off. This solid is washed with water then set aside. The organic phase of the mother liquor is separated, then washed with brine, dried over MgSO4 and concentrated to give a solid. This material is 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 is washed with water
  3. customThe organic phase of the mother liquor is separated
  4. washwashed 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-58bbc339f9dc41b992642b35114e9bf1
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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