Ethylene Glycol → 2-(5-tert-Butyl-2-methoxy-3-nitro-phenyl)-[1,3]dioxolane

Participants

Reaction Steps

A solution of 1.0 g (4.2 mmol) of 5-tert-Butyl-2-methoxy-3-nitro-benzaldehyde, 1.18 mL of ethylene glycol, and 0.4 g of pTSA hydrate in 50 mL of benzene was refluxed for 24 h under Dean-Stark conditions. The benzene was evaporated and the resultant oil was redissolved in EtOAc. The organic layer was washed with water, sat'd NaHCO3, and brine. The extract was dried over MgSO4, filtered, and concentrated. Chromatography (10% EtOAc in hexanes) provided 1.0 g of 2-(5-tert-Butyl-2-methoxy-3-nitro-phenyl)-[1,3]dioxolane as a light yellow oil.

Provenance & Evidence