A dry THF (30 mL) solution of 2,6-di-tert-butyl-4-thiocyanatophenol (10.0 g, crude) was slowly added dropwise to a suspension of tetrahydrolithium aluminum (2.0 g, 52.6 mmol) in THF (50 mL) at 0 C. The reaction was kept at 0 C for 5 h. The reaction was quenched by the slow addition of EtOAc (20 mL), followed by the addition of 3NHCl (50 mL), EtOAc (200 mL), and partitioning of the organic phase. The organic phase was washed with saturated NaHCO3 and brine, respectively, and dried over anhydrous sodium sulfate. The crude product was passed over a chromatographic column (silica gel, EtOAc: PE = 1:10 to 1:5) to give the product 2,6-di-tert-butyl-4-mercaptophenol (5.4 g), a yellow waxy solid.
