Ethylene Glycol → HCID 774818, compound

Participants

Reaction Steps

Methyl 4-formylbenzoate (3.28 g, 20.0 mmol) was suspended in ethylene glycol (4.46 mL, 80.0 mmol), then successively treated with triethyl orthoformate (3.66 mL, 22.0 mmol) and Me3NPhBr3 (376 mg, 1.00 mmol) at 22° C.; within 5 min, all solids dissolved. The resulting orange solution was stirred 0.5 h, then diluted with saturated aqueous NaHCO3 (50 mL), transferred to separatory funnel and washed with EtOAc (3×50 mL). The combined EtOAc washes were dried over MgSO4, filtered and concentrated in vacuo to a colorless oil (Rf 0.4 in 4:1 pentane/EtOAc, KMnO4). This material was used without further purification in the subsequent reduction step.

Provenance & Evidence