Water → Phenol, 4,4'-tellurobis-

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Reaction Steps

Silyl ether 4b (54.2 g, 0.1 mol) was taken up in methanol (200 mL) in a 500 mL round bottom flask. Potassium fluoride (11.6 g, 0.2 mol) was added, and the reaction was heated to reflux for 1.5 h under argon. After the reaction was cooled to rt, it was poured into rapidly stirring water (1.2 L), using additional methanol (20 mL) to facilitate the transfer. The pH was adjusted to 14 with 10% NaOH (approx. 40 mL), and the reaction was filtered through Celite diatomaceous earth. The filtrate was transferred to a separatory funnel and washed twice with dichloromethane. The aqueous layer was transferred to a 2 L Edenmeyer flask in an ice bath, and 25% aq. acetic acid was added to pH 6, resulting in formation of a cream-colored precipitate. The product was isolated by filtration, washed with water, and air dried, to give the crude product (29 g). It was adsorbed onto flash silica gel (150 mL) using ether. Vacuum chromotography on 1 L flash silica gel, eluting with dichloromethane then 1:4 ethyl acetate:dichloromethane gave the pure product. Trituration with dichloromethane gave, in two crops, pure 4c as a yellow solid (24 g, 76%). 1H NMR (CDCl3, 5 drops DMSO) δ8.77 (2H, s), 7.29 (4H, d, J=8.4), 6.47 (4H, d, J=8.4).

Provenance & Evidence