Hydrochloric Acid → 2-(4-Hydroxyphenyl)indole

Participants

Reaction Steps

4-Hydroxyacetophenone phenylhydrazine (47 g.) was fused with 250 g. zinc chloride (10 min. at 180° C.), poured into 3 1. of 0.3 N HCl, heated and stirred for one hour on the steam bath, cooled to 0° and filtered. The precipitant was extracted with boiling pet. ether and allowed to stand. 2-(4-Hydroxyphenyl)indole (17 g., m.p. 224°-229°) was isolated. A well-stirred mixture of 2-(4-hydroxyphenyl)indole (0.1 mole), iodoethane (0.1 mole) and sodium bicarbonate (0.12 mole) in 200 ml. of acetone was refluxed overnight. After 400 ml. of water was added, the product 2-(4-hydroxyphenyl)-1-ethylindole (A) was filtered out. Then A was reacted with 4,4'-bis(2-bromoethoxy)-2-hydroxybenzophenone as in Example 1 to produce Compound VII.

Provenance & Evidence