O-Methylthiomethyl phenol

An alternative approach is also feasible. The phenol is treated with the complex of NCS and dimethyl sulfide (4, 87-90) to give the azasulfonium salt (d), which is converted as shown to the o-methylthiomethyl phenol (4). ... 

Reactions of (1) and (2) with phenols give o-methylthiomethylated phenols (eq 2). Mixtures of the phenols and 0.5 equiv of (1) or (2) are heated without solvent at 120-130 °C for 3-7 h. 2-Methylthiomethylphenols are obtained from 2- and 4-methyl, 2,5- and 3,5-dimethyl-, 2,3,5-trimethyl-, and 2-methoxyphenols in 55-95% yield (Table 2). In some case, significant amounts of bis(methylthiomethyl) products are also formed. The yields using (2) are higher than those using (1). 

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