Aluminium lithium hydride → 2,2-Ditetradecylpropane-1,3-diol

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Reaction Steps

LAH (9.68 mmol) is added to a diethyl-2,2-ditetradecylmalonate (2.42 mmol) solution in THF at rt and the reaction mixture is heated under reflux for 2 h. The reaction mixture is quenched with 1 M HCl solution and stirred for 30 min. The aqueous layer is extracted with diethyl ether two times. The combined organic layers are washed with a dilute HCl solution and brine, and then dried over anhydrous magnesium sulfate. Solvents are evaporated under vacuum. The reaction afforded 2,2-ditetradecyl-1,3-propanediol in 91% yield 1H NMR (300 MHz, CDCl3): δ 3.57 (s, 4H, CH2O), 1.38-1.15 (m), 0.88 (t, 6H, J=8.0 Hz).

Provenance & Evidence