3971-29-7

85-42-7

3971-29-7

The general procedure for the synthesis of 1,2-cyclohexanedimethanol from hexahydrophthalic anhydride (mixture of isomers, 5.00 g, 32.0 mmol) is as follows: an anhydrous tetrahydrofuran (30 mL) solution of hexahydrophthalic anhydride was slowly added dropwise to an anhydrous tetrahydrofuran (200 mL) suspension of lithium aluminium hydride (4.21 g, 110 mmol) at 0 °C. The reaction mixture was then heated to 60 °C and maintained for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and crushed ice was carefully added to quench the excess lithium aluminum hydride. The precipitate was removed by filtration and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried and the solvent evaporated. The crude product was ground in ether to give the target product in 75% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.36-1.55 (m, 8H), 1.91-1.96 (m, 2H), 2.76 (br s, 2H, disappeared after D2O exchange), 3.58 (dd, J = 11.0 and 4.1 Hz, 2H), 3.77 ppm (dd, J = 11.0 and 8.2 Hz. 2H). Mass spectrum (ESI): m/z 145 [M + H]+, 167 [M + Na]+. The IR spectrum shows an absorption peak at ν3389 cm-1. Elemental analysis results: calculated values (C8H16O2): C, 66.63%; H, 11.18%. Measured values: C, 66.57%; H, 11.16%.