4-Chloro-3-methoxybenzoic acid → (4-Chloro-3-methoxyphenyl)methanol
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH3:12]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 4-chloro-3-methoxybenzoic acid (4.88 g, 26.2 mmol) in THF (50 mL) was added borane-THF complex (52 mL 1M solution in THF, 52 mmol) via addition funnel over 10 min. The reaction mixture was refluxed for 2 hr, cooled, extracted with EtOAc, washed with water, 5% Na2CO3 and brine, dried and concentrated in vacuo to give (4-chloro-3-methoxyphenyl)methan-1-ol (4.5 g, 99%). ES-MS (M+H−H2O)+=155, 157 (Cl).
Aufarbeitung
- additionvia addition funnel over 10 min
- temperatureThe reaction mixture was refluxed for 2 hr
- temperaturecooled
- extractionextracted with EtOAc
- washwashed with water, 5% Na2CO3 and brine
- customdried
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-c262f28a375b4b27b75682ab1f478255
- Quelldatensatz
- uspto-grants-2011_11
- Patentnummer
- US08067428B2
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