Methyl iodide → 3-(Trimethylsilyl)phenol

Participants

Reaction Conditions

Reaction Steps

Next, a dry 3 l, 3-neck flask, equipped with a mechanical stirrer and reflux condenser, and connected to a mineral oil bubbler, was flushed with a stream of argon. The flask was charged with substituted phenol (B) (200 g, 800 mmol), fresh magnesium turnings (21.6 g, 0.89 mol), THF (900 ml), and maintained at about 0° C. in an ice bath. Methyl iodide (2 ml) was added as the catalyst to initiate reaction. The reaction was kept under control by carefully applying and removing the ice bath as necessary to counter the significant heat generated. The resulting mixture was gently heated to reflux for 30 min to drive the reaction to completion, as evidenced by the dissolution of the magnesium. Once again the mixture was cooled to 0° C. in an ice bath, and chlorotrimethylsilane (133.5 g, 1.2 moles) was added. The resulting mixture was gently refluxed and monitored by thin layer chromatography (TLC) to completion. The mixture was subsequently cooled to about 0° C., and 800 ml of water was slowly added to hydrolyze the silyl ether and magnesium salts. The organic layer was separated, washed with 2×100 ml portions of brine and dried over sodium sulfate. Removal of the volatile solvents provided 3-trimethylsilylphenol (C) as a yellow oil, further purified by flash chromatography (ligroin 950:ether=15:1) 116 g, 85% yield).

Provenance & Evidence