Boron trifluoride etherate → 2-(2-(Hydroxymethyl)-5-nitrophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a Tetrahydrofuran (THF) (220 mL) solution of 2-carboxymethyl-4-nitro-benzoic acid (10.0 g, 44.4 mmol) was added sodium borohydride (5.06 g, 133 mmol) in portions. The contents were cooled to 0° C., and boron trifluoride diethyl etherate (21.3 mL, 133 mmol) was added dropwise over 1 hr. The contents were allowed to warm to 25° C. and stirred for 16 hrs. The reaction was cooled to 0° C. and cautiously quenched with aqueous sodium hydroxide (1 N, 178 mL). The contents were stirred for 3 hrs, THF was removed under vacuum, the resulting aqueous suspension was cooled to 0° C. and the product was filtered off. After drying, the product was obtained as a white solid 7.78 g (89%, mp 79-81° C.). IR 3277, 3192, 2964, 2932, 1614, 1525, 1507, 1170, 1134, 1089, 1067 cm-1.1H NMR (CD3)2SO δ8.05 (d,J=9 Hz, 1H), 8.04 (s, 1H), 7.66 (d, J=9 Hz, 1H), 5.42 (t,J=5 Hz, 1H), 4.74 (t, J=5 Hz, 1H), 4.64 (d, J=5 Hz, 2H), 3.63 (m, 2H), 2.80 (t, J=6 Hz, 2H). 13C NMR (CD3)2SO δ149.1, 146.6, 139.2, 127.8, 124.3, 121.3, 61.2, 60.6, 34.9. Anal. Calcd for C9H11NO4 :C, 54.82; H, 5.62; N, 7.10. Found: C, 54.54; H, 5.49; N, 7.07.

Provenance & Evidence