Hydrochloric Acid → 22-Hydroxydocosanoic acid

참여 물질

반응 조건

반응 단계

22-Hydroxy-docosanoic acid was synthesized according to Mori et al., Liebigs Ann. Chem., (1991), 253-257. Briefly, under N2 atmosphere 6.6 g Docos-21-enoic acid ethyl ester and 30 ml THF were combined and cooled down to 0° C. Then 0.5 eq. (9 ml) borane/THF complex was added dropwise and the mixture was allowed to stir for 2 hours at room temperature. After the addition of 1.2 ml H2O the suspension was again cooled down to 0° C. and 15 ml 3M NaOH and 2 ml 35% H2O2 were added. The mixture was stirred for one hour at 50° C. Then the temperature was brought to room temperature and the pH was adjusted to pH 2-3 with 2N HCl. The solid was fritted, washed with H2O, codistilled three times with CHCl3 and recrystallized from CHCl3. After a further treatment with NaOH (3M in H2O) in THF at 50° C. over 1.5 days the pH was again adjusted to pH 2-3 and the crude product was fritted, washed with H2O and codistilled two times with CHCl3. The product was characterized by thin layer chromatography and 1H-NMR.

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