Reaktionsgleichung
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:23]=[CH:22][C:11]([CH2:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.C1C[O:27]CC1>>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[O:27])=[CH:22][CH:23]=1Komponenten
Versuchsvorschrift
A 1 M solution of lithium aluminum hydride in THF (258 ml, 258 mmol) was added dropwise to a solution of the mixture of 2-(4-fluorobenzyl)benzoic acid and the starting material 2-(4-fluorobenzoyl)benzoic acid, which was isolated in step 1, in THF (200 ml). The reaction mixture was heated to reflux for 2 hours. It was cooled to 0° C. Carefully, methanol (100 ml) and water (50 ml) were added successively. A 10% aqueous solution of sodium hydrogensulphate (500 ml) and a 1 N solution of sodium chloride in water were added. The phases were separated. The aqueous phase was extracted with ethyl acetate (2×300 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (600 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. 5.23 g of [2-(4-fluorobenzyl)phenyl]methanol were isolated by flash chromatography on silica (200 g), using ethyl acetate/heptane 1:1 as eluent.
Quellen und Nachweise
- ORD-Eintrag
- ord-28a1ae342895478ba3f040c84ef89aea
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06610721B2
Verknüpfte Notizen
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