Methanol → Methyl 3-ethylbenzoate

Reaktionsgleichung

OS(O)(=O)=O.[CH2:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12])[CH3:7].[CH3:17]O>O>[CH2:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([O:13][CH3:17])=[O:12])[CH3:7]

Komponenten

Versuchsvorschrift

Concentrated H2SO4 (1.0 mL) was added to a solution of 3-ethylbenzoic acid (500 mg, 3.33 mmol) in MeOH (10 mL). The mixture was heated at reflux for 18 h then cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with Et2O (3×100 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by chromatography on silica gel (hexanes→20% EtOAc/hexanes, gradient) afforded 500 mg (91%) of methyl 3-ethylbenzoate.