Ethyl (R)-3-hydroxybutyrate

Description

Ethyl (R)-(-)-3-Hydroxybutyrate is a chiral starting material for the production of numerous biologically active compounds.

Chemical properties

clear colorless liquid

The Uses of Ethyl (R)-3-hydroxybutyrate

Ethyl (R)-(-)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds used in the pharmaceutical industry. It is formed during the hydrolysis of poly-3-hydroxybutyrate.

Definition

ChEBI: Ethyl (R)-3-hydroxybutanoate is an ethyl 3-hydroxybutyrate. It is functionally related to a (R)-3-hydroxybutyric acid.

General Description

Ethyl (R)-3-hydroxybutyrate is an enantiomer of 3-hydroxybutyric acid. It is synthesized from diethyl succinate in a one-pot, stereoselective, high-yield process by using asymmetric synthesis and hydrogenation. The reaction vessel used for this synthesis is a reaction solution that has been optimized to be resistant to high pressure and temperature. This product can be used as a renewable feedstock in the production of polyesters and other polymers.

Synthesis

(R)-β-Butryrolactone (20 g, 230 mmol) was dissolved in 500 mLethanol with 1.0 mL H2SO4 and stirred at room temperature. Aliquots(100 μL) were added to 1.0 mL of methanol and analyzed by GC-MS for conversion of the lactone. Upon completion (> 48 h), a small amount of solid sodium bicarbonate was added and the solvent removed by rotary evaporation. The residue was taken up in dichloromethane and washed with water. The water layer was extracted twice with ethyl acetate. The pooled organic layers were dried with magnesium sulfate, which was then filtered and the solvent removed by rotary evaporation to yield Ethyl (R)-3-hydroxybutyrate as a clear oil (20.2 g, 66%).