Toluene → HCID 9840004, compound

Participants

Reaction Steps

A 12.5% solution of phosgene in toluene (10.7 mL, 12.0 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide in tetrahydrofuran (200 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and aqueous sodium bicarbonate. The organic phase is washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a crude product which is crystallized from hexane to afford 1.6 g (74%) of 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethyl]-1,3,4-oxadiazol-2(3H)-one, mp 120.0°-123.0° C.

Provenance & Evidence