Dibenzothiophene → 4-Hydroxydibenzothiophene

Participants

Reaction Steps

n-Butyllithium (26.25 g, 406 mmols, 175 ml of 2.4M solution in hexane) was added to a stirred solution of dibenzothiophene (25 g, 135.7 mole) in dry THF (200 ml) at 0° C. over a period of 1 hr under dry N2 atmosphere. This reaction mixture was stirred overnight at room temperature and dry oxygen gas was bubbled into the reaction mixture over 5 hrs. This reaction mixture was poured slowly over cold 1N HCl (500 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×500 ml). Organic layers were mixed together and concentrated to dryness to get crude product (32 g). The crude product was purified by silica gel column chromatography.

Provenance & Evidence