Reaktion #76229

Reaktionsgleichung

1-(benzyloxy)-2-naphthaldehyde

sodium borohydride

→

[1-(benzyloxy)-2-naphthyl]methanol

Ausbeute 99.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is removed in vacuo
2. 2
   Sonstigeto give a crude solid which
3. 3
   Sonstigeis partitioned between ethyl acetate (300 mL) and water (300 mL)
4. 4
   SonstigeThe organic layer is separated
5. 5
   Waschenwashed with water (300 mL), aqueous sodium chloride (300 mL)
6. 6
   Trocknendried (magnesium sulfate)
7. 7
   Filtrationfiltered through a plug of silica (10 cm×5 cm)
8. 8
   SonstigeThe solvent is removed in vacuo

Vorschrift

To a solution of 1-(benzyloxy)-2-naphthaldehyde (7.00 g, 26.7 mmol) in methanol (250 mL) at 0° C. is added sodium borohydride (1.51 g, 40.0 mmol) and the reaction mixture is allowed to stir at room temperature for 24 h. The solvent is removed in vacuo to give a crude solid which is partitioned between ethyl acetate (300 mL) and water (300 mL). The organic layer is separated and washed with water (300 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate) and filtered through a plug of silica (10 cm×5 cm). The solvent is removed in vacuo to give 6.98 g (99%) of [1-(benzyloxy)-2-naphthyl]methanol as white crystalline solid. Rf=0.36 (silica, dichloromethane:hexanes 3:2); mp 85-87° C. Anal. Calcd. for C18H16O2: C, 81.24; H, 6.14. Found: C, 81.03; H, 5.98.

Quelle