p-Toluenesulfonic acid → Methyl 3-formylpicolinate

HRID 1493138Notes

Reaction equation

HRID 1493138 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11](OC)[O:12]C)=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11]=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10856765HCID 10856765, compound

Product 1

HCID 10877473Methyl 3-formylpicolinate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(dimethoxymethyl)-2-pyridinecarboxylic acid methyl ester (1.02 g) in dioxane (20 mL) was added water (20 mL), followed by p-toluenesulfonic acid (0.3 g). This solution was heated at 55°-60° C. for 24 hours. The reaction mixture was cooled, diluted with water (50 mL), treated with aqueous saturated sodium bicarbonate until the pH was 7.5-8.0, and extracted with methylene chloride (3×). The combined organic extracts were washed with dilute brine (3×), dried (K2CO3) and evaporated to afford a light yellow solid which yielded 540 mg (62.5%) of an almost pure product.

Workup

  1. temperatureThis solution was heated at 55°-60° C. for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with methylene chloride (3×)
  4. washThe combined organic extracts were washed with dilute brine (3×)
  5. dry with materialdried (K2CO3)
  6. customevaporated
  7. customto afford a light yellow solid which
  8. customyielded 540 mg (62.5%) of an almost pure product

Sources & evidence

ORD record
ord-7ee0b79668d147dab5772abbd6744e18
Source dataset
uspto-grants-1991_06
Patent number
US05021418

Reaction notes

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