Triethylamine → Methyl 5-formyl-2-methanesulfonyloxybenzoate

HRID 2221595Notes

Reaction equation

HRID 2221595 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(OCC)(=O)C>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14363598Methyl 5-Formylsalicylate

Product 1

HCID 23076526Methyl 5-formyl-2-methanesulfonyloxybenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 5-formyl-2-hydroxybenzoate (21.76 g), triethylamine (13.46 g), ethyl acetate (300 mL) was added dropwise methanesulfonyl chloride (15.24 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. The reaction mixture was washed successively with water, saturated aqueous sodium hydrogen carbonate, 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 5-formyl-2-methanesulfonyloxybenzoate as a colorless oil (31.20 g, yield 100%).

Workup

  1. washThe reaction mixture was washed successively with water, saturated aqueous sodium hydrogen carbonate, 1N hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a52da7cf307c4afa81e4a5b0c41e419a
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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