Boron trifluoride etherate → 2-(2-(Hydroxymethyl)-5-nitrophenyl)ethanol
Reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[OH:8][CH2:7][C:6]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:5]=1[CH2:4][CH2:1][OH:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- temperatureto warm to 25° C.
- temperatureThe reaction was cooled to 0° C.
- customcautiously quenched with aqueous sodium hydroxide (1 N, 178 mL)
- stirringThe contents were stirred for 3 hrs
- customTHF was removed under vacuum
- temperaturethe resulting aqueous suspension was cooled to 0° C.
- filtrationthe product was filtered off
- customAfter drying
Sources & evidence
- ORD record
- ord-06b9f6325a2440149a8e892f4b810374
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968950
Reaction notes
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