4-Propylguaiacol → 4-Propyl-1,2-benzenediol

Participants

Reaction Conditions

Reaction Steps

To 38 mg (0.23 mmole) of 2-methoxy-4-propylphenol in 0.4 ml of CH2Cl2 at −78° C. and under argon was added 254 μl (0.252 mmole) of a IM BBr3 solution in CH2Cl2. The reaction mixture was stirred at −78° C. for one hour and then warmed to 0° C. The reaction was quenched by addition of 2 ml of water. The mixture was extracted three times with 5 ml of CH2Cl2, dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was flash chromatographed over silica gel using 25% ethyl acetate in hexane to furnish 30 mg of 2-hydroxy-4-propylphenol, Structure (I-6), in 86% yield.

Provenance & Evidence