Acetone → Methyl 2,2-dimethyl-4-oxochroman-6-carboxylate

Participants

Reaction Steps

Methyl 3-acetyl-4-hydroxybenzoate (200 mg, 1.03 mmol), acetone (151 μL, 2.06 mmol) and pyrrolidine (25.6 μL, 0.31 mmol) were mixed in toluene (515 μL) and stirred at room temperature for 1 hour. It was then heated to 100° C. for 5 hours, allowed to cool to room temperature, diluted with EtOAc (50.0 mL) and poured into ice. The two layers were separated. The organic layer was washed with 2 N aqueous HCl (10.0 mL), 2 N aqueous NaOH (10.0 mL), water (10.0 mL), dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-30% EtOAc/hexanes to give the desired product as a pale-yellow oil.

Provenance & Evidence