Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[BH4-].[Na+].CO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2.3 g, 8.7 mmol) in tetrahydrofuran (10 mL) was treated with sodium borohydride (0.496 g, 13 mmol) and heated to refluxing temperature. The reaction mixture was then treated drop wise with methanol (1 mL) and continued refluxing for about 2 hours. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride solution followed by partitioning with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography using ethyl acetate in hexane (10%) as an eluant to yield methyl 2,6-dichloro-4-(hydroxymethyl)benzoate as a colorless liquid (1.6 g, 80%).
Aufarbeitung
- temperatureheated
- temperatureto refluxing temperature
- temperaturecontinued refluxing for about 2 hours
- customquenched with saturated aqueous ammonium chloride solution
- customby partitioning with ethyl acetate
- washThe combined organic layer was washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-6dc1f2d7982d47929c08e708e487565d
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08980911B2
Verknüpfte Notizen
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