Ethanol → HCID 14360127, compound

Participants

Reaction Steps

Twenty grams of bakers' yeast (Sigma Chemical Company, type II) was suspended in an aqueous solution containing 30 grams of sucrose in a conical flask, and the mixture was placed on an orbital shaker (220 rpm) at 30° C. for 30 minutes to initiate fermentation. Two grams of octyl 2-ethyl acetoacetate was dissolved in 2 ml of 95% ethanol, the resulting solution was added to the fermenting yeast, and shaking was resumed. The reaction was followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After approximately 48 hours the reaction was judged complete, and the reaction was terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension was suction filtered through a pad of Celite and the clear yellow filtrate was extracted with ethyl acetate (4×200 ml). The extracts were combined, dried over MgSO4, filtered, and rotary evaporated to leave 1.8 grams of octyl (2R,3S)-2-ethyl-3-hydroxybutyrate as a yellowish oil (>96% enantiomeric excess as judged by chiral chromatography).

Provenance & Evidence