Acetonitrile → 1-((2-Ethylhexyl)oxy)-4-methoxybenzene

Participants

Reaction Steps

A mixture of 4-methoxyphenol (100.0 g), dry potassium carbonate (166.7 g), acetonitrile (800 mL), and 2-ethylhexyl bromide (173.8 g) was stirred mechanically and heated at reflux for 4 days. The mixture was then allowed to cool to room temperature and was diluted with 1.5 L of deionized water, after which the organic phase was separated. The aqueous phase was extracted with hexane, and the combined organic layers were washed two times with a 1.0 moles/liter aqueous solution of NaOH and were then dried over MgSO4. The solvent was removed under reduced pressure to give an orange oil. The crude product was distilled under reduced pressure to give 152 g of a clear oil (bp 135-138° C. at 0.4 mmHg).

Provenance & Evidence