Acetic Anhydride → Acetic acid N-hydroxysuccinimide ester

Participants

Reaction Steps

N-Hydroxysuccinimide (17.33 g, 0.5 mol) was suspended in 120 ml tetrahydrofuran and cooled in an ice bath. Acetic anhydride (16 ml, 0.17 ml) and then triethylamine (22 ml, 0.16 mol) were added slowly. A solution formed, and then gradually a white precipitate appeared. After one half hour an equal volume of petroleum ether was added, and the crystalline product was collected. Yield 21.22 g (90%, mp 128°-130° C., lit. 15 mp 131°-132° C.). Analysis (C6H7NO4): calc. 45.87% C, 4.49% H, 8.91% N; found 45.86%, C, 4.31% H, 8.61% N.

Provenance & Evidence