(R)-(-)-3-Hydroxytetrahydrofuran

Chemical Properties

Uses

Uses

Synthesis

125605-10-9

86087-24-3

Example 5 Preparation of (R)-3-hydroxytetrahydrofuran: 35 g (0.28 mol) of (R)-4-chloro-1,3-butanediol made in reference to Example 2 was dissolved in 70 mL of 0.5 N hydrochloric acid solution and the reaction was heated under reflux conditions for 2 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was neutralized with 50% aqueous sodium hydroxide solution, followed by evaporation under reduced pressure to remove water. To the residual crystals and oily mixture, 60 mL of methanol was added and mixed with thorough stirring. Insoluble crystals were removed by filtration and the filtrate was concentrated under reduced pressure. Finally, the concentrated residue was distilled under reduced pressure to give 16.6 g of (R)-(-)-3-hydroxytetrahydrofuran in the form of colorless liquid (purity: 99.1%; yield: 67%). Its rotundity was determined as [α]D23 = -15.91° (c = 2.45, methanol).

References