N-Hydroxyphthalimide → Phthalimidyl 10-hydroxydecanoate

Participants

Reaction Steps

To a solution of 10-hydroxydecanoic acid (1.880 g, 10 mmol) in dichloromethane (25 mL) at room temperature was added N-hydroxyphthalimide (NHP) (1.63 g, 10 mmol) followed by N, N′-dicyclohexylcarbodimide (DCC) (2.1 g, 10 mmol). Quantitative conversion to product was achieved after stirring at room temperature for 45 minutes as determined by tlc using silica gel (ethyl acetate/heptane 4:1; Rf=0.28). The precipitate was removed by filtration and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel column (2.5×30 cm) using chloroform/methanol (98:2) to give 1.7 g product (yield 52%) as a colorless syrup.

Provenance & Evidence