Preparation of 6-isopropyl-3-methyl-4-thiocyanatophenol (4-hydroxy-2-methyl-5-(propan-2-yl)phenyl thiocyanate)
15 g of thymol and 35 g of sodium thiocyanate dihydrate are dissolved in 150 ml of methanol saturated with sodium bromide. 20 g of bromine in 30 ml of methanol saturated with sodium bromide is added to this solution at room temperature with stirring. After 30 min a six- to eight-fold amount of water is added, whereupon the 6-isopropyl-3-methyl-4-thiocyanatophenol separates as an oil. 6-Isopropyl-3-methyl-4-thiocyanatophenol crystallizes in 2 hours at 0° C, is dried, and after recrystallization with charcoal from light petroleum yields 95% of 6-isopropyl-3-methyl-4-thiocyanatophenol, which has m.p. 105° C.
J. Chem. Soc, 1949, 1855;
J. Amer. Chem. Soc, 72, 3704, (1950).