Reactions of 3-Hexene. II. Condensations with Aromatic Hydrocarbons and Phenols

Abstract

Vol. 61 to keep the reaction mixture strongly alkaline. The mixture is heated for one hour longer, cooled and extracted with ether. The ether is evaporated and the material is vacuum distilled; yield 138 g., b. p. 105°( 16 mm.). m-Methoxyphenethyl Alcohol.-A Grignard reagent is prepared from 17 g. of magnesium, 120 g. of m-bromoanisole and 400 cc. of anhydrous ether. When the magnesium has almost completely dissolved, 35 g. of ethylene oxide (excess) in twice its volume of ether is added through the dropping funnel, cooling the flask in running water.The mixture is refluxed for thirty minutes; 200 cc. of benzene (anhydrous) is added, about three-fourths of the ether is distilled off, and the residue is refluxed for one hour longer (temperature 60°). The mixture is decomposed with diluted sulfuric acid in crushed ice. The ether layer is dried with sodium sulfate, and the ether is evaporated. The residue is vacuum distilled: b. p. 148°( 13 mm.); yield 60 g.

Properties of Alkylbenzenes.

“…The following hydrocarbons listed in a compilation or abstract must be considered unknown, since the names apply to alkylbenzenes described apparently correctly by the original authors under different names: "1,2-di-n-propylbenzene" (95, 137); "3-methyl-4-phenylhexane" (4); "2-p-tolylhexane" (95,344); "1-propyl-2-n-pentylbenzene" (43, 95); "l,3,5-trimethyl-2-(2'-metbylbutyl)benzene" (95,199); "l-methyl-3,5-di-n-butylbenzene" (95,257); "3-propyl-3-phenylheptane" (95, 138); "l-methyl-5-undecylbenzene" (87,140); "1,4-di-sec-hexylbenzene" (95, 344); "2,8-dimethyl-3-propylnonane" (95, 138); "5-phenyl-2,8-dimethyl-8-isobutylnonane" (87,138). This would apply also to "2-phenyl-3methylhexane" (87,138), except that it was probably present in one of the products of Huston and Kaye (156).…”