2-tert-Butyl-4-methylphenol → HCID 178426895, compound

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of nitrogen, 16.42 g (100 mmol) of 2-tert-butyl-4-methylphenol was dissolved in 100 ml of diethyl ether and 33.3 ml of methylmagnesium bromide (100 mmol of diethyl ether solution) was added dropwise to this at 0° C. taking 5 minutes. After completion of the dropwise addition, the mixture was stirred at 25° C. for 10 minutes. After that, the diethyl ether was evaporated under vacuum, and 150 ml of toluene was added to obtain a toluene solution of 2-tert-butyl-4-methylphenoxymagnesium bromide. To the solution, 5.61 g (50 mmol) of 2-thiophenecarboxyaldehyde was added dropwise at 25° C. After stirring for 24 hours, 5% aqueous hydrochloric acid solution was added and aqueous layer was separated. After the organic layer was washed with a saturated aqueous sodium chloride solution, it was dried with anhydrous magnesium sulfate and the solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (a developing solvent: hexane/ethyl acetate=30/1) to obtain 2-bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methylthiophene in a yield of 63%.

Provenance & Evidence