Methanesulfonic Acid → 4,7-Di-t-butyl-5-hydroxy-2-n-octyl-2,3-dihydrobenzofuran

Participants

Reaction Conditions

Reaction Steps

Under ice-cooling, 1.5 ml of methanesulfonic acid was added dropwise to a solution of 0.51 g of 4-t-butyl-5-hydroxy-2-n-octyl-2,3-dihydrobenzofuran in 0.85 g of t-butyl alcohol and 2 ml of chloroform. After stirring at 0° C. for 15 minutes, the mixture was poured into ice water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane) to give 0.35 g of 4,7-di-t-butyl-5-hydroxy-2-n-octyl-2,3-dihydrobenzofuran as a pale yellow oil (yield 58%).

Provenance & Evidence