GB875464A - Process for the production of hydroxyaryl-alkyl thioethers - Google Patents

Abstract

Hydroxyaryl alkyl thioethers are prepared by reacting an aromatic hydroxy compound having at least one free p-position or one free o-position with an alkyl sulphenyl halide. The alkyl sulphenyl halide may be prepared in situ by the action of a sulphuryl halide or an an alkyl thiol or a dialkyl disulphide. The reaction may be carried out at temperatures in the range -20 DEG to 50 DEG C. in the presence or absence of inert diluents such as toluene, chloroform, chlorobenzene, xylenes or tetrachlorethane and condensation agents such as hydrochloric acid, benzene sulphonic acid, zinc chloride or boron trifluoride. Since a hydrogen halide is evolved small quantities of water may be added to the reaction mixture. In the examples methyl sulphenyl chloride is reacted with phenol to give 4-hydroxy-1-methylmercapto benzene, m-cresol to give 3-hydroxy-6-methylmercapto toluene, m-chlorophenol to give 3-hydroxy-6-methylmercapto-chlorobenzene; sulphuryl chloride and di-methyl disulphide are reacted with phenol, o-cresol to give 2-hydroxy-5-methylmercapto toluene, p-cresol to give 4-hydroxy-5-methyl-mercapto toluene, m-cresol, m-chlorophenol, 4-chloro-2-hydroxy toluene to give 2-hydroxy-4-chloro-5-methylmercapto toluene, 6-chloro-3-hydroxy toluene to give 3-hydroxy-4-methyl-mercapto - 6 - chlorotoluene, phenol in the presence of ferric chloride and phenol in the presence of water; sulphuryl chloride and methyl mercaptan are reacted with phenol; sulphuryl chloride and di-n-butyl disulphide are reacted with phenol to give 4-hydroxy-n-butylmercapto benzene and using diethyl di-sulphide 4-hydroxy-ethylmercapto benzene is obtained; sulphuryl chloride and dimethyl di-sulphide are reacted with b -naphthol to give 1-methylmercapto - 2 - hydroxy-naphthalene; methyl sulphuryl chloride and dimethyl di-sulphide are reacted with resorcinol to give 2,4-dihydroxy-1-methylmercapto-benzene.