Reaktion #317304

Reaktionsgleichung

4-(diethyoxymethyl)benzaldehyde

NaBH4

→

4-(hydroxymethyl)benzaldehyde

Ausbeute 89.4%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe MeOH was removed
2. 2
   workup.ADDITIONdiluted with water
3. 3
   ExtraktionThe aqueous layer was extracted with DCM (3×50 mL)
4. 4
   SonstigeThe combine organic layers were dried
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   workup.DISSOLUTIONThe crude oil was dissolved in MeOH (50 mL)
8. 8
   workup.ADDITIONTo this was added 2N HCl (10.0 mL) in ether
9. 9
   workup.WAITThe reaction mixture was left at room temperature for 24 hours
10. 10
    SonstigeThe MeOH was removed
11. 11
    Sonstigethe crude product was purified by flash column chromatography
12. 12
    Wascheneluting with EtOAc/Hexane (3:7)

Vorschrift

To a cold (0° C.) solution of 4-(diethyoxymethyl)benzaldehyde (5.2 g, 24 mmol) in MeOH (50 mL) was added NaBH4 (0.93 g, 24 mmol), and the reaction mixture was stirred for 3 hours. The MeOH was removed and the residue was taken up in DCM and diluted with water. The aqueous layer was extracted with DCM (3×50 mL). The combine organic layers were dried, filtered and concentrated. The crude oil was dissolved in MeOH (50 mL) and cooled to 0° C. To this was added 2N HCl (10.0 mL) in ether. The reaction mixture was left at room temperature for 24 hours. The MeOH was removed and the crude product was purified by flash column chromatography, eluting with EtOAc/Hexane (3:7) to yield 2.92 g of 4-(hydroxymethyl)benzaldehyde (11) as a colorless oil.

Quelle