Hydrochloric Acid → Methylcreosol (mixed isomers)

Participants

Reaction Steps

A mixture of 10 mL of CH2Cl2, 10 mL of H2O, 460 mg of 2,6-dimethylhydroquinone, 200 mg of NaOH, 940 mg (2 eq) of methyl iodide, and 760 mg of benzyl triethyl ammonium bromide in CH2Cl2 /H2O (C) were stirred at room temperature under argon for 12 hr. Dilute HCl was added to adjust the pH to 7.0, followed by 200 mL of CH2Cl2, and the organic layer was extracted with brine (5×100 mL), dried over Na2SO4, the solvent evaporated under reduced pressure, and the crude product was applied to silica gel (230-400 mesh, CH2Cl2) to yield 356 mg of product 25, about 70% yield.

Provenance & Evidence