Ethylene Glycol → 2-[2-[3-(1,1-Dimethylethyl)phenyl]ethyl]-1,3-dioxolane

Participants

Reaction Steps

Ethylene glycol (15 mL, 0.27 mol, 1.2 eq), paratoluene sulfonic acid (430 mg, 1% w/w) and cyclohexane (50 mL) were charged into a 1 L three-necked round-bottom flask, equipped with a dean and stark, a reflux condenser and a mechanical stirrer. 3-(3-tert-butylphenyl)propanal (50.6 g, gc purity of 85%, 0.22 mol) was added dropwise at ambient temperature. After stirring for 2 h at reflux, the reaction mixture was cooled to ambient temperature and washed twice with water (50 mL), saturated aqueous NaHCO3, dried over magnesium sulphate and concentrated to give 2-[2-(3-tert-butylphenyl)ethyl]-1,3-dioxolane in the form of a pale yellow coloured oil (60 g, gc purity>84%; yield>95%). The material was used as such for the next step.

Provenance & Evidence