Sodium Hydroxide → p-Phenylenebis(dimethylsilanol)

Participants

Reaction Steps

Into a flame dried 250 mL three neck round bottom flask equipped with magnetic stirrer and water condenser was added anhydrous ethanol (122 mL) and a small piece of sodium metal under argon. The ethanol was heated to reflux. Then, the 1,4-bis(dimethylsilyl)benzene (100 g, 51.5 mmol) was added dropwise to the reaction flask with stirring over 30 minutes. When hydrogen evolution ceased, the reaction mixture was added with vigorous stirring to a mixture of NaOH (69.45 g), CH3OH (427 mL) and H2O (48.8 mL). After standing for 15 min, another solution of NaOH (69.45 g) in H2O (463.6 mL) was added to the mixture. The mixture was allowed to stand for 30 minutes with occasional shaking and then poured into a vigorously stirred solution of KH2PO4 (610 g) in excess ice and H2O (2440 mL). Crude disilanol product was precipitated as a white solid, filtered, dissolved in ethyl ether (610 mL), and washed with an equal volume of water. The ether solution of the product was dried (anhydrous Na2SO4) and concentrated to give a white solid. The solid was recrystallized from hot CCl4 (500 mL) and dried at 60° C. overnight in vacuo to provide final needle-like white solid product (90 g, yield 77.6%). 1H and 13C NMR analyses were consistent with the structure assigned.

Provenance & Evidence