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

HRID 2184211

Reaktionsgleichung

Reaktionsgleichung von HRID 2184211
[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-c5b88d121e2e44029ae58041f92e0a19
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900231B2

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