Dicyclohexylcarbodiimide → Pentafluorphenyl 6-octyloxy-2-naphthoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-octyloxy-2-naphthoic acid (3.15 g, 10.5 mmol) and dicyclohexylcarbodiimide in ethyl acetate (25 ml) at 0° C. was added pentafluorophenol (2.12 g, 11.5 mmol). The mixture was stirred at 25° C. for a period of 18 h. The precipitate was removed by filtration. The filtrate was washed with water (2×150 ml) and brine and dried with magnesium sulfate. Removal of the ethyl acetate in vacuo gave 5.4 g of pentafluorphenyl 6-octyloxy-2-naphthoate as a solid: 1H NMR (400 MHz, CD3OD) δ0.88 (t, 3H, J=6.9 Hz), 4.10 (t, 2H, J=6.6 Hz), 7.16 (d, 1H), 7.21 (d, 1H), 7.80 (d, 1H), 7.87 (d, 1H), 8.08 (dd, 1H), 8.69 (d, 1H).

Provenance & Evidence