Methyl 2-methoxy-3-nitrobenzoate → (2-Methoxy-3-nitrophenyl)methanol
Reaktionsgleichung
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[O:13][CH3:14].[BH4-].[Na+]>C(O)(C)(C)C>[CH3:14][O:13][C:5]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 14.0 g of 2-methoxy-3-nitro-benzoic acid methyl ester in 245 ml of tert-butanol was treated with 6.75 g of sodium borohydride, and the heterogeneous mixture to 80° C. Methonol (62 ml) was slowly added at a dropwise rate over 2 hr. After 3 hr at 80° C., the solvent was evaporated at 40° C. under reduced pressure and the residue was treated with water, acidified with hydrochloric acid, extracted with ethyl acetate, the extracts washed with brine, dried, and evaporated to dryness. Purification of the residue by flash column chromatography on silica gel afforded 8.3 g of (2-methoxy-3-nitro-phenyl)-methanol as a brown solid. ##STR157##