Process for preparing meta-alkyl-chloro- and fluorophenols

1,170,037. m-Alkylhalophenols. CHEVRON RESEARCH CO. 10 April, 1968 [20 April, 1967], No. 17388/68. Heading C2C. The invention relates to a method of preparing a m - alkylfluoro or m - alkylchlorophenol which comprises reacting a hydrocarbon monoalkene having from 3 to 15 carbon atoms, e.g. 1- butene, isobutene, 2-pentene, propene or 1- dodecene with a halophenol, e.g. 2-chlorophenol, 4 - chlorophenol, 3 - chlorophenol, 2 - fluorophenol or 4-fluorophenol the halogen in the latter being fluorine or chlorine respectively, in the presence of an acid-activated Group II metal montmorillonite clay at a temperature in the range of from 110‹ to 155‹ C. for a time sufficient to alkylate the halophenol in either the ortho or para position relative to the hydroxyl group and thereafter increasing the temperature to from 165‹ to 195‹ C. for a time sufficient to isomerize the alkylate into the corresponding m-alkylfluoro or m-alkylchlorophenol. In an example 2- chlorophenol is reacted in the presence of a calcium montmorillonite clay with 1-butene at 140‹ to 150‹ C. after which the temperature was raised to 185‹ to 190‹ C. and subsequently the clay filtered from the reaction mixture leaving 5-see-butyl-2-chlorophenol.