Sodium Hydroxide → 6-bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene

Participants

Reaction Conditions

Reaction Steps

4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene (293 mg, 1.03 mmol) dissolved in dichloromethane (3.10 mL) was cooled to 0° C. and aluminum chloride (138 mg, 1.03 mmol) in dichloromethane (3.0 mL) was added via a syringe. The reaction mixture was stirred at 0° C. for 30 minutes. It was then poured into an Erlenmeyer flask containing a 10% aqueous NaOH solution and ice. The mixture was extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-10% EtOAc/Hexanes to give the title compound as a colorless oil.

Provenance & Evidence