Hydrogen Peroxide → HCID 21288128, compound

Participants

Reaction Steps

To a solution of 33.8 g (0.174 moles) of 2-ethenyl-4-methoxy-1-O-methoxymethylphenol in 300 ml of dry tetrahydrofuran at 0° was added 120 ml of a 1.0M borane-tetrahydrofuran solution. The solution was stirred at room temperature for 60 minutes, cooled to 0° and 48 ml of 10% NaOH was added dropwise. Then 41 ml of 30% H2O2 was added with caution and the mixture was stirred at room temperature for 30 minutes. The solution was partitioned between ether and water and the ether layer was washed with aqueous NaHCO3 and brine, dried (Na2SO4) and evaporated. The oily residue was purified by Prep. 500 HPLC using 40% ethylacetatehexane to afford 27.3 g (73%) of 2-(2-hydroxyethyl)-4-methoxy-1-O-methoxymethylphenol as a colorless liquid.

Provenance & Evidence