Ammonium Hydroxide → HCID 11024571, compound

Participants

Reaction Steps

The ester of Example 5c (2R-trans)-(2-napththalenyl) 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate (462 g, 1 mol) was dissolved in acetone (5 L) and ammonium hydroxide (1 L). After stirring briefly at room temperature the reaction mixture was heated to reflux for 20 minutes, recooled to room temperature and concentrated to 1/3 of the original volume on the rotary evaporator. The solution was diluted with toluene (10 L) and washed with 10% aq. NaOH (3×5 L), water (1×5 L) and brine (1×5 L). The toluene solution was further evaporated to a volume of 2.5 L and n-hexane (7.5 L) was added. Upon cooling in the refrigerator (~12 h), the solid was collected and dried to yield the titled oxiranecarboxamide (302 g, 86%). Mp 81°-82° C.; [α]D +13.2° (c 1, CH2Cl2, 25° C.), [α] 546 +16.1.

Provenance & Evidence