Reaction with phenylmagnesium bromide. A solution of 2.5 g. of III in 10 ml. of benzene was treated with 6 ml. of 2N ethereal phenylmagnesium bromide, giving a deep purple solution and a gummy black precipitate that dissolved when the mixture was kept overnight. Addition of dilute hydrochloric acid, etc. gave 2.9 g. of a pale tan oil that could not be obtained crystalline. This was treated with 10 ml. of 20% methanolic potassium hydroxide, rapid solution occurring, followed by separation of a colorless crystalline potassium salt. This salt was washed with methanol and then ether, then dissolved in water and acidified. The resulting 1,3-diphenyl-l-hydroxyindene-H-carboxylic acid separated as an oil, which crystallized after it had been kept under ether-ligroin for several days. Recrystallization from dilute alcohol gave fine colorless needles, m.p. 163-164°. The compound gave a deep purple color with coned, sulfuric acid Anal. Caled, for C22HAO3: C, 80.5; , 4.91. Found: C, 80.6; H, 4.92. A solution of 0.5 g. of this acid in 5 ml. of acetic acid and 1 ml. of acetyl chloride was treated with 0.5 g. of zinc dust and boiled for 10 min. Water and ether were then added, and the ether solution was extracted with dilute sodium carbonate. This removed 50 mg. of 1,3-diphenylindene-$carboxylic acid, flat yellow needles from dilute acetic acid, m.p. 195-196°that gave no color with coned, sulfuric acid.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
customersupport@researchsolutions.com
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.