Sodium hydride → HCID 23017946, compound

Participants

Reaction Steps

To a solution of 5.0 g (36.7 mmol) of 3,5-dimethylanisole in carbon tetrachloride (35 mL) was added 5.2 g (29.4 mmol) of N-bromosuccinimide and 0.2 g (0.74 mmol) of benzoyl peroxide at room temperature, followed by heating under reflux for 2 hours. The reaction mixture was left standing to cool and then filtered. The filtrate was concentrated under a reduced pressure. The obtained residue was dissolved in ethanol (7.5 mL), and treated with 4.5 g (26.1 mmol) of 4-methylsulfonylphenol and 7.5 mL (30.0 mmol) of a 4 N aqueous sodium hydride, and heated under reflux for 1 hour. After standing to cool, water and hexane was added to the reaction mixture, and the precipitates were collected by filtration and washed with ether. The residue was purified by column chromatography (silica gel 80 g, developing solvent: chloroform-ethyl acetate=4: 1) to obtain 4.5 g (yield 40.4%) of 1-(4-methanesulfonylphenoxymethy)-3-methoxy-5-methylbenzene (VI-7) as a colorless crystal. Its physical properties are shown below.

Provenance & Evidence