Reaktion #439003

Reaktionsgleichung

NaOH

LiAlH4

ethyl 3,4-(methylenedioxy)benzoate

→

desired product

Ausbeute 94.5%

3,4-(Methylenedioxy)phenylmethanol

Ausbeute 94.5%

Lösungsmittel

Et2O

H2O

THF

H2O

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeobtained in the preceding section)
2. 2
   workup.ADDITIONwas added under argon
3. 3
   FiltrationThe resulting mixture was filtered
4. 4
   Waschenwashed with Et2O and EtOAc
5. 5
   Sonstigethe solvent was evaporated
6. 6
   SonstigeThe residue was partitioned between H2O and EtOAc
7. 7
   Sonstigethe layers were separated
8. 8
   Extraktionthe aqueous phase was extracted with EtOAc
9. 9
   Trocknenthe combined organic phases were dried over MgSO4
10. 10
    Einengenconcentrated

Vorschrift

To a mixture of 0.99 g (26.16 mmol) of LiAlH4 and 80 mL of Et2O, 2.54 g (13.08 mmol) of ethyl 3,4-(methylenedioxy)benzoate (obtained in the preceding section) dissolved in 160 mL of Et2O was added under argon, and the mixture was stirred overnight at room temperature. A mixture of 1.62 mL of H2O and 3.41 mL of THF, followed by 1.62 mL of 15% NaOH and then 4.43 mL of H2O were added dropwise. The resulting mixture was filtered, washed with Et2O and EtOAc, and the solvent was evaporated. The residue was partitioned between H2O and EtOAc, the layers were separated, the aqueous phase was extracted with EtOAc and the combined organic phases were dried over MgSO4 and concentrated, yielding 1.88 g of the desired product (94% yield).

Quelle