P-Ethylbenzyl chloride

A mixture of 500 g. (4.7 moles) of ethylbenzene, 60 g. (2.0 moles) of paraformaldehyde, and 40 g. of anhydrous pulverized zinc chloride is stirred, and the temperature held at 60° while a stream of dry hydrogen chloride is passed through the reaction mixture. Hood.) Introduction of the gas is continued as long as any is absorbed (about 20 minutes). The upper layer is separated and washed once with water, then several times with dilute sodium carbonate solution, followed by drying over calcium chloride. Distillation of the resulting product gives 200 g. (65%) of p-ethylbenzyl chloride boiling at 95-96°/15 mm. 

---

Ci3Hi80, Mr 190.29, does not occur in nature. It is a colorless liquid, df 0.951-0.959, j) 1.504-1.509, with a powerful, clean, fresh air tone, reminiscent of ocean breeze. It can be prepared by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of catalysts. The product is used in perfumes for, e.g., household products. 

Reactive halogen compounds such as benzyl chloride, 2-thenyl chloride, 2-bromoacetylthiophene, (C HjS)COCH,Br , and 2-chloromethyl-thianaphthene (C,H5S)CHjCl are readily converted to esters by treatment with the sodium salts of carboxylic acids. A small amount of tri-ethylamine has proved to be an effective catalyst. Acetates are oftentimes made by heating halides with fused sodium acetate in glacial acetic acid, e.g., p-ethylbenzyl acetate (93%). The reaction is of little value for the preparation of simple aliphatic esters. Secondary and tertiary halides give increasing amounts of olefin by dehydro-halogenation. 

Ethylbenzyl chloride Ethylene dibromide V,V -Dinitroethylenediamine Hexaethyl tetraphosphate M ethylbenzyl alcohol m-Benzenedisulfonic acid Methylbenzyl chloride V-Bromosuccinimide Octamethyl pyrophosphoramide p-Aminosalicylic acid Pentaerythritol tetranitrate Tris-(/3-chloroethyl) amine Tetraethylammonium bromide Tetraethyl pyrophosphate 2,2,6,6-Tetramethylolcyclohexanol... 

Acetoxy-2,4-dimethyl-m-dioxane Alkyl dimethyl ethylbenzyl ammonium chloride p-Anisic acid Benzoic acid p-Bromo-3-nitrostyrene... 

Sodium dimethyidithiocarbamate n-Tetradecyl dimethyl ethylbenzyl ammonium chloride antimicrobial, surfactants p-Anisic acid... 

Acenaphthene 6-Acetoxy-2,4-dimethyl-m-dioxane Alkyl dimethyl ethylbenzyl ammonium chloride 2-Amino-4-chloro-6-nitrophenol Ammonium polysulfide Ammonium thiosulfate Anilazine Aniline Arsenic pentoxide Basic yellow 2 Bromoacenaphthylene 3-Bromochloro-5,5-dimethyl hydantoin p-Bromo-p-nitrostyrene Cadmium Cadmium chloride Calcium oxide Calcium polysulfide Carvacrol Cetalkonium chloride Cetethyidimonium bromide... 

---