Hexadecanolide → 16-Hydroxyhexadecanoic acid

Reaktionsgleichung

[C:1]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:19].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:17])=[O:18]

Komponenten

Versuchsvorschrift

A 5 liter three neck round bottom flask, equipped with a mechanical stirrer and reflux condenser, was charged with 300 g (1.16 moles) of 99% hexadecanolide, 1000 mls of 50% sodium hydroxide, 1500 mls of toluene and 5.6 g (0.01 6 moles) of 97% tetrabutylammonium hydrogen sulfate. The reaction mixture stirred at 85°-95° C. overnight, the reaction was cooled, and filtered under vacuum. The filtered solid was washed with diethyl ether before being added to water and acidified to pH=1.5 with concentrated hydrochloric acid. The precipitated product was filtered under vacuum, washed several times with water and dried at 50°-60° C. under high vacuum to give 353 g (1.2 moles) of 97% 16-hydroxy hexadecanoic acid.