Methanesulfonyl chloride → Methyl 4-methyl-3-[(methylsulfonyl)oxy]benzoate
Reaktionsgleichung
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][S:14]([CH3:13])(=[O:16])=[O:15]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of methyl 3-hydroxy-4-methylbenzoate (3.0 g, 18.1 mmol) in pyridine (20 mL) was added methanesulfonyl chloride (2.80 mL, 36.1 mmol) under stirring at 0° C., and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (4.11 g, yield 93%) as a yellow oil.