Citric Acid → (3R)-3-Hydroxydecanoic acid

Participants

Reaction Steps

Baker's yeast (Saccharomyces cerevisiae, Malteserkors®, De danske Spritfabrikker, 640 g), D-glucose (720 g), potassium dihydrogenphosphate (1.6 g) and magnesium sulfate (0.8 g) in water (2 l) were stirred at room temperature for 30 minutes. A solution of the above potassium 3-oxodecanoate in water (1.5 l) was added. The mixture was stirred at ambient temperature and pH was kept between 6.0 and 6.5 by automatic titration with 1M potassium hydroxide or 1M citric acid. After 48 hours Celite® was added, and after stirring for 30 minutes more the mixture was filtered. The filtrate was acidified to pH 2.5 with concentrated hydrochloric acid, extracted with methylene chloride (2×2 l), dried and evaporated in vacuo to give crude 3(R)-hydroxydecanoic acid.

Provenance & Evidence