Hydrochloric Acid → 3-Hydroxybutyrate thiophenyl ester

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Reaction Steps

In a dry flask on ice, 6 ml of dehydrated dichloromethane was stirred and 2 ml of 2M trimethyl aluminum was slowly added thereto under a nitrogen stream. After that, 2 mmol of thiophenol was slowly added thereto. The mixture was stirred at room temperature for 30 minutes and then 3-hydroxybutyrate dissolved in 6 ml of dehydrated dichloromethane was added thereto. The reaction was monitored by a TLC. To this mixed solution was added 20 ml of dichloromethane and, until generation of bubbles stopped, 20 ml of 3% hydrochloric acid solution was added. The mixed solution was transferred to a separating funnel, washed with 3% hydrochloric acid solution for two times and with saturated saline for two times, dried over magnesium sulfate and evaporated in vacuo to give 532 mg of crude oily 3-hydroxybutyrate thiophenyl ester in dark yellow color. This was purified by a column chromatography (20 cm×1 cm diameter; eluent was hexane:ethyl acetate=2:1) using silica gel 60 to give 125 mg of pure 3-hydroxybutyrate thiophenyl ester as a transparent oil. The yield to the unpurified substance was 24%. Result of NMR analysis of this compound is as follows.

Provenance & Evidence