CIS-1,4-CYCLOHEXANEDIOL

cis-1,4-Cyclohexanediol is a metabolite of the side-chain of candesartan cilexetil (C175580), on digoxin-induced arrhythmias in dogs with congestive heart failure.

Crystallise the cis-diol from acetone (charcoal), then dry and sublime it under vacuum. It also crystallises from Me2CO or Me2CO/*C6H6. The diacetate has m 40.6-41.1o (from pet ether or 34-36o from EtOH). [Grob & Baumann Helv Chim Acta 38 604 1955, Owen & Robins J Chem Soc 320 1949, Beilstein 6 III 4080, 6 IV 5209.]

Chair conformation:
this form of cis-1, 4-cyclohexane diol is most stable,

there will be a strong intramolecular hydrogen bonding. In cyclohexane boat form 1, 4 interaction is know as Flagpole interaction which makes it unstable. But in this case, ?OH groups are present instead of hydrogen and there will be a strong hydrogen bonding and no flagpole interaction. Hence, diaxial boat form is more stable.