Hydrochloric Acid → 2-Cyano-2-methylhexyl p-toluenesulfonate

Participants

Reaction Steps

535 mg (3.8 mM) of (-)-2-cyano-2-methylhexanol ([α]435 -1.9 degree (c=2.393, methylene chloride)) and 911 mg (11.4 mM) of dry pyridine were stirred at room temperature, followed by addition of 724 mg (3.8 mM) of p-toluenesulfonyl chloride and 7 hours of reaction. After the reaction, 6 ml of 2M-hydrochloric acid was added and extraction with ether was effected. The organic layer was washed with a small amount of 2M-hydrochloric acid and distilled water, followed by drying on sodium sulfate and distilling-off of the solvent under reduced pressure The product was then purified by thin layer chromatography (developer solvent: hexane/methylene chloride=1/5) to obtain 748 mg of (+) 2-cyano-2-methylhexyl p-toluenesulfonate. Yield: 63.3%, [α]D +10.7 degrees (c 2.182, benzene).

Provenance & Evidence