Pyridine → 1,1-Dimethylethyl 4-methylbenzoate

Reaktionsgleichung

[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:12]1([CH3:21])[CH:17]=[CH:16][C:15]([C:18](Cl)=[O:19])=[CH:14][CH:13]=1>O>[CH3:21][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])=[CH:14][CH:13]=1

Komponenten

Versuchsvorschrift

37 g of tert-butanol and then 26 ml of pyridine are added to 39.04 g of p-toluoyl chloride and the reaction mixture is refluxed for 3 hours. After cooling, it is poured into water, extracted with AcOEt, washed with a 1N solution of HCl and then with a 5% solution of sodium hydrogencarbonate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using hexane and then a hexane/DCM mixture (80/20; v/v) as the eluent to give 38.9 g of the expected product, which is used as such in the next step.