Hydrochloric Acid → 2,6-Di-tert-butyl-4-({[dodecyl(dimethyl)silyl]methyl}sulfanyl)phenol

Participants

Reaction Steps

Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10 mmol), potassium carbonate (1.7 g, 12.3 mmol), chloromethyldodecyldimethylsilane (2.8 g, 10 mmole) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water, acidify with aqueous hydrochloric acid and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through fluorosil-Na2SO4 and evaporate to an orange semi-solid (4.0 g). Purify the product by first distilling (180°-200° C. @0.1 mm Hg) then subjecting to silica gel chromatography (CCl4) to obtain the title compound as a colorless oil which slowly crystallizes.

Provenance & Evidence