Borane → (2-Methyl-5-nitrophenyl)methanol

HRID 1060229

Reaktionsgleichung

Reaktionsgleichung von HRID 1060229
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Komponenten

6

Edukt 3

HCID 6331BoraneHCID 11430Potassium CarbonateHCID 5196832-Methyl-5-nitrobenzoic acid

Produkt 1

HCID 3567085(2-Methyl-5-nitrophenyl)methanolAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Methyl-5-nitrobenzoic acid (2.00 g, 11.0 mmol) was warmed under nitrogen, dissolved in anhydrous THF (25 mL), and treated with a 1N solution of borane in THF (16.5 mL). After stirring 18 hours at ambient temperature the reaction was quenched with a solution of potassium carbonate (1.8 g, 13 mmol) in water (50 mL), and the THF removed in vacuo. The remaining aqueous solution was extracted with DCM, and the organic layer washed with pH 7 buffer and brine, dried over sodium sulfate, and filtered. The evaporated filtrate gave the title compound as a pale yellow solid (1.76 g, 95%). 1H NMR (300 MHz, CDCl3) δ 8.29 (d, 1H, J=2.5 Hz), 8.04 (dd, 1H, J=8.3 Hz, 2.5 Hz), 7.31 (d, 1H, J=8.31 Hz), 4.77 (d, 2H, J=5.5 Hz), 2.41 (s, 3H), 2.09 (t, 1H, J=5.6 Hz).

Aufarbeitung

  1. customthe THF removed in vacuo
  2. extractionThe remaining aqueous solution was extracted with DCM
  3. washthe organic layer washed with pH 7 buffer
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-6a4e6d6f47e94bbd8cef11feb56f19bf
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521663B2

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