Studies of Conjugated Systems. Vii. The Chemical Reactions of the Geometric Isomers of Methylstyrylcarbinol

Abstract

I may be decomposed directly with a saturated solution of sulfurous acid and thus avoid the preliminary treatment with dilute acid. After all of the iodine had been removed the ethereal solution was washed with water until neutral. A large number of washings were required to remove all of the sulfurous acid. The ethereal solution was dried over sodium sulfate and the ether removed by vaporization. When subjected to distillation under reduced pressure, the residual oil distilled over almost completely at 117°under 4 mm. pressure. It was identical with the trans carbinol described above.The Preparation of Cis Methylstyrylcarbinol.-The above preparation was repeated except that the ethereal solution of the carbinol was washed only twice with water before distillation, thus leaving some of the sulfurous acid in solution. On distilling the residual oil, the cis methylstyrylcarbinol was obtained, b. p. 144°under 21 mm. pressure. It was identified by its characteristic tendency to lose water.