Sodium Iodide → Tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methane

Participants

Reaction Steps

Trimethylsilyl chloride (68.1 mL, 539 mmol) and sodium iodide (81.0 g, 540 mmol) were mixed in acetonitrile (500 mL), and tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol (62.4 g, 90.2 mmol, Example 44) and was added with efficient stirring at room temperature. The reaction flask was surrounded with aluminum foil to prevent light to enter. After stirring for 24 h, the reaction mixture was poured into 2 L of a Na2S2O3 solution (70 g of Na2 S2O3 ×5H2O in 2 L of water). A yellow precipitate was formed, filtered off and was left to dry on the filter under suction (2 h). The product was triturated with i-PrOH twice, filtered and washed with cold diisopropyl ether (15 mL) to yield 54.1 g (88%) of the product tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methane.

Provenance & Evidence