Hydrochloric Acid → (+/-)-9,9'-spirobixanthene-1,1'-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2 (1.0 g, 2.3 mmol) in dry toluene (20 mL) was added AlCl3 (1.9 g, 14.3 mmol). The solution was warmed slowly and refluxed for 30 minutes. Then it was cooled to 0° C. and concentrated aqueous HCl (20 mL) was introduced with vigorous stirring. After refluxing for 1 hour, the reaction mixture was extracted with EtOAc, washed with concentrated HCl, water, aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated. Flash chromatography (eluting with CH2Cl2) gave 3 as light-yellow powder (0.64 g, yield 72%).

Provenance & Evidence