Hydrochloric Acid → HCID 17959616, compound

Participants

Reaction Steps

5 g (13.3 mmol) of 1,8-dibromo-3,6-di-tert-butylxanthene together with THF were placed in a reaction vessel under argon. At −50° C., 12.3 ml (30.7 mmol) of a 2.5 molar n-butyllithium solution in hexane were added. The reaction mixture was stirred for 2 hours, resulting in formation of a colorless suspension. At 0° C., 100 ml (100 mmol) of a 1 molar solution of BH3 in THF were added dropwise and the mixture was stirred overnight at 5–15° C. It was subsequently carefully hydrolyzed at 0° C. using 25 ml of water. 3 N KOH (7.4 g of KOH in 32 g of H2O) and 10.4 g of 30% strength H2O2 solution were carefully added to the reaction mixture and the resulting mixture was refluxed for 2 hours. After cooling to room temperature, it was neutralized using 18% strength hydrochloric acid. After phase separation, the organic phase was washed twice with NaCl solution, dried over Na2SO4 and evaporated to dryness. 1,8-Dihydroxy-3,6-di-tert-butylxanthene was obtained in a yield of 4.7 g (100% of theory).

Provenance & Evidence