Ethanolamine → HCID 86622007, compound

Participants

Reaction Steps

To a 500 mL round bottom flask equipped with stirbar, Dean-Stark apparatus, reflux condenser, and N2 inlet was added benzophenone (45.5 g, 0.25 mol), ethanol amine (23 mL, 0.38 mol), p-toluenesulfonic acid (4.3 g, 0.025 mol), and toluene (300 mL). The reaction stirred at reflux for 16 hours, collecting 8 mL water. The solution was cooled and the solution washed with NaHCO3(aq) (2×400 mL). The aqueous layer was extracted with ether (2×300 mL) and the combined organic layers dried over MgSO4, stirred with carbon black for 1 hour, then filtered. The solvent was evaporated and the residue dissolved in ether (300 mL). Hexanes (900 mL) was added and the product crystallized over 2 hours at room temperature. The solid was filtered and recrystallized from 3:1 hexanes:ether giving 25.2 g of colorless needles (0.112 mol, 45%). HPLC (3:1 acetonitrile:water, C8 column) 99.9+% pure.

Provenance & Evidence