2-Allylphenol → (2,3-Dihydro-1-benzofuran-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of meta-chloroperbenzoic acid (96.4 g, 335 mmol) in dichloromethane (500 mL) was added to an ice-cold solution of 2-allylphenol (30 g, 224 mmol) in dichloromethane (1 L) and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 18 hours. The reaction mixture was then re-cooled to 0° C., quenched with 2M sodium hydroxide solution (700 mL) and stirred for 30 minutes. The organic layer was then separated, dried over magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil was purified by HPLC using a Chiralpak AD 250*4.6 mm column and hexane:isopropanol (90:10) as the eluant, to afford the title compound.

Provenance & Evidence