Lithium aluminum hydride → Rac-(1s,4s)-4-(hydroxymethyl)cyclohexanol

Temperature

0 °C

Ethyl 4-oxocyclohexanecarboxylate (2.0 g, 0.012 mol) was dissolved in ether (20.0 mL) and was then cooled at 0° C. Into the mixture was added 1 M lithium tetrahydroaluminate in ether (20 mL) and the resulting mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water (2 mL) and 1 N NaOH (2 mL) and ether was added (100 mL). The precipitated solids were filtered off and the residue was used in the next reaction. 1H NMR (CDCl3): δ 4.02 and 3.75 (m, 1H), 3.45-3.61 (m, 2H), 2.02 (m, 2H), 1.84 (m, 1H), 1.52-1.80 (m, 2H), 1.44 (m, 1H), 1.32 (m, 2H), 1.03 (m, 1H).

1. customThe reaction was quenched with water (2 mL) and 1 N NaOH (2 mL) and ether
2. additionwas added (100 mL)
3. filtrationThe precipitated solids were filtered off
4. customthe residue was used in the next reaction

ORD record

ord-ff8014134170435393a9436ab470ad49

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530485B2