Pyridine → 2-Formylphenyl methanesulfonate

HRID 1854696Notes

Reaction equation

HRID 1854696 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl.C(OCC)(=O)C>[CH3:16][S:17]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6998SalicylaldehydeHCID 31297Methanesulfonyl chloride

Product 1

HCID 144443722-Formylphenyl methanesulfonateYield 98.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxybenzaldehyde (0.30 mL, 2.8 mmol) and pyridine (0.91 mL, 11.2 mmol) in 5.6 mL of dichloromethane was added methanesulfonyl chloride (0.65 mL, 8.4 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was diluted with ethyl acetate. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 50/50) to obtain the title compound as a white solid (553 mg, 98%).

Workup

  1. washThe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 50/50)

Sources & evidence

ORD record
ord-613e329dd1984791b098f910f7d727f3
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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