A mixture of triphenylphosphine (5 mmol) and menthol (5 mmol) in acetone (15 mL) was cooled to -10C. With stirring at -10C, a small portion of NBS (5 mmol) was added to this cooled mixture. After complete addition of NBS, the temperature was allowed to rise to room temperature and polymer-loaded thiolated resin (6 g, 6 mmol) was added to the reaction mixture. It was then stirred for 10 min. After completion of the reaction (TLC), the resin was filtered and washed with acetone (3 x 10 mL). The solvent was removed under vacuum to obtain menthol thiol which was further purified by column chromatography. The title compound 4-methoxybenzyl mercaptan was obtained in 94% yield.
