Water → 5-Chloromethyl-3-[4-(1-methylethyl)phenyl]-2-oxazolidinone

Participants

Reaction Conditions

Reaction Steps

0.2-0.3 grams of lithium chloride was added to a solution of 7 grams (0.076 mole) epichlorohydrin in 30 ml dimethylformamide at 90° C. Heating was discontinued, and a solution of 12.25 grams (0.076 mole) 4(1-methylethyl)phenylisocyanate in 10 ml dimethylformamide was added dropwise at such a rate that the reaction temperature did not exceed 110° C. When the addition was complete heat was reapplied and the reaction solution was stirred at 90° C. for 3 hours. The solution was then added in a slow stream to a vigorously stirred mixture of ice and water, about 200 ml total volume. The reaction product solidified and was recovered by filtration. Recrystallization from methanol afforded an 85% yield of white crystalline material (mp 77°-79° C.).

Provenance & Evidence