9798. Tryptophol

Nomenclature

CAS number: 526-55-6
3-Indoleethanol; 3-ω-hydroxyethylindole; 2-(3-indolyl)ethyl alcohol; 2-indolyl(3)-ethanol; β-indolylethyl alcohol; 3-β-hydroxyethylindole.
C10H11NO; mol wt 161.20.
C 74.51%, H 6.88%, N 8.69%, O 9.93%.

Description and references

Prepd by treatment of indolemagnesium bromide with ethylene oxide: Oddo, Cambieri, Gazz. Chim. Ital. 60, 19 (1939); Snyder, Pilgrim, J. Am. Chem. Soc. 70, 1962 (1948); by Bouveault-Blanc reduction of 3-indoleacetic ester: Jackson, J. Biol. Chem. 88, 659 (1930); by treatment of indolemagnesium iodide with ethylene chlorohydrin: Majima, Hoshino, Ber. 58, 2042 (1925); from gramine: Snyder, Pilgrim, J. Am. Chem. Soc. 70, 3770 (1948). By lithium aluminum hydride reduction of methyl 3-indoleglycolate: Speeter, Anthony, US 3076814 (1963 to Upjohn).

Chemical structure

Properties

Platelets from ether + petr ether, mp 59°. bp2.0 174°. Slightly sol in water. Sol in methanol, ethanol, ether, acetone, chloroform, ethyl acetate, glacial acetic acid. Moderately sol in benzene, amyl alcohol, hot carbon disulfide. Sparingly sol in petr ether.