3-Bromo-2,5-dimethoxybenzaldehyde → 3-Bromo-2,5-dimethoxybenzyl Alcohol

HRID 1835994

Reaktionsgleichung

Reaktionsgleichung von HRID 1835994
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Komponenten

4

Edukt 2

HCID 9310963-Bromo-2,5-dimethoxybenzaldehydeHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 101927773-Bromo-2,5-dimethoxybenzyl AlcoholAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of 51 (8.0 g, 33 mmol) in THF (100 ml) was added LiAlH4 (15 ml of 1.0M in THF) dropwise. After 15 min, the reaction was quenched with 2N HCl and the aqueous layer was extracted with EtOAc. The EtOAc layer was dried concentrated to give a solid (7.5 g, 93%): Mp=65-67° C.; 1H NMR (DMSO-d6) δ 7.05 (d, 1 H, J=3.0 Hz), 6.98 (d, 1 H, J=2.5 Hz), 5.28 (t, 1 H, J=4.9 Hz), 4.47 (d, 2 H, J=5.7 Hz), 3.73 (s, 3 H), 3.67 (s, 3 H); MS 245 (M−H)−

Aufarbeitung

  1. customthe reaction was quenched with 2N HCl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe EtOAc layer was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f03923f1153f4479855097c93705d95a
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774248B2

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