Toluene → 3-[4-(3-Chlorobenzyloxy) phenyl] 5-(1-hydroxyethyl) oxazolidin-2-one

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Reaction Steps

From a solution of 600 ml of toluene containing 33.4 g (0.10 mol) of the mixture obtained in Example 2, 150 ml of solvent is distilled in an argon atmosphere. Then, successively, 15 g (15.5 ml; 0.127 mol) of ethyl carbonate and 3.4 ml of a solution of EtONa in 1M anhydrous EtOH are added. After 4 hrs 30 mins of reflux, the cyclization reaction is complete. The reaction medium is concentrated, then taken up by 300 ml of methyl ethyl ketone. After washing with 2N HCl, then with a saturated NaCl solution, 35 g of brown solid is recovered corresponding to the product expected.

Provenance & Evidence