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

Temperature

-78 °C

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.

1. temperaturewarmed to 0° C
2. customThe reaction was quenched by addition of 2 ml of water
3. extractionThe mixture was extracted three times with 5 ml of CH2Cl2
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated by rotary evaporation
6. customchromatographed over silica gel using 25% ethyl acetate in hexane

ORD record

ord-50cff2c174a2427981ee3a4766fdd1d9

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06498191B2