1,1-Bis(hydroxymethyl)cyclopropane

Chemical Properties

Uses

Synthesis

6914-71-2

39590-81-3

The general procedure for the synthesis of 1,1-cyclopropanedimethanol from dimethyl 1,1-cyclopropanedicarboxylate was as follows: lithium aluminum hydride (LiAlH4, 569 mg, 15.0 mmol) was added batchwise to a solution of dimethyl-1,1-cyclopropanedicarboxylate (791 mg, 5.01 mmol) in ether (Et2O, 20 mL) at 0 °C. The reaction mixture was stirred at room temperature for 4 h. The reaction was subsequently quenched with saturated sodium sulfate (Na2SO4) solution at 0 °C. The precipitated solid was filtered and washed with tetrahydrofuran (THF). The filtrate was concentrated and purified by column chromatography (eluent: ethyl acetate, EtOAc) to afford 440 mg (86% yield) of the target product 1,1-cyclopropanedimethanol. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 4.02 (s, 2H), 3.56 (s, 4H), 0.48 (s, 4H); mass spectrum (electrospray ionization, ES) m/z: 125 ([M + Na]+).

References