Ethylene Glycol → HCID 66936799, compound

Participants

Reaction Steps

To a solution of the relevant spiro[5.5]undec-7-en-2-one isomer (10) or (10′) (10 g, 61 mmol) in toluene (150 mL) was added HO(CH2)2OH (10 mL, 179 mmol) and p-toluenesulfonic acid H2O (0.57 g, 3 mmol). The reaction mixture was brought to reflux and the H2O generated was removed by azeotropic distillation (using a Dean-Stark separator). The reaction mixture was then cooled and washed with a saturated NaHCO3 solution. The aqueous phase was extracted with Et2O and the combined organic layers dried over anhydrous Na2SO4. The solvent was removed in vacuo and the resulting residue purified over silica (isooctane/EtOAc, 95:5) to afford 12.1 g (95% yield) of the desired product which was characterized as follows:

Provenance & Evidence