Aluminium lithium hydride → [1-(Hydroxymethyl)-4,4-dimethoxycyclohexyl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-ethyl 1-methyl 4,4-dimethoxycyclohexane-1,1-dicarboxylate (4.7 g, 17.13 mmol) in dry Et2O (250 mL) at 0° C. was added LiAlH4 (17.1 mL of a 2 M solution in THF; 34.3 mmol) dropwise over 15 min. The reaction mixture was stirred at 0° C. for 15 min, then warmed to rt and stirred for 1 h. It was then cooled to 0° C. and carefully quenched with aqueous NaOH (7.3 mL of a 1N solution; 7.3 mmol). The mixture was filtered and the filtrate was concentrated in vacuo to afford the title compound (3.6 g, 100% yield) as a semisolid. 1H NMR (500 MHz, CDCl3) δ 3.65 (d, J=4.4 Hz, 4H), 3.20 (s, 6H), 2.42 (t, J=4.6 Hz, 2H), 1.67 (dd, J=7.3, 4.9 Hz, 4H), 1.53-1.41 (m, 4H).

Provenance & Evidence