Hydrochloric Acid → 5-Hydroxymethyl-1-naphthaldehyde

HRID 1166793

Reaktionsgleichung

Reaktionsgleichung von HRID 1166793
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]([O:15]C)=O)#N.CC(C[AlH]CC(C)C)C.Cl.C1C[O:30]CC1>>[OH:15][CH2:13][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:3]2[CH:1]=[O:30]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 826304Methyl 5-cyano-1-naphthoate

Produkt 1

HCID 110195775-Hydroxymethyl-1-naphthaldehydeAusbeute 91 %

Versuchsvorschrift

To a cooled (0° C.) solution of methyl 5-cyano-1-naphthylcarboxylate (1 g, 5 mmol) in 20 mL anhydrous THF was added DIBAL (1M in hexane, 20 mL, 20 mmol) via syringe. The mixture was then kept between 50-60° C. overnight. The mixture was then cooled to room temperature. The mixture was poured into a cold (0° C.) solution of 2 N HCl (100 mL). The product was extracted with ether (2×). The organic layer was washed with brine, dried over MgSO4 and concentrated. Silica gel column chromatography using hexane/ethyl acetate (2/1) gave the 0.85 g (91%) of the product.

Aufarbeitung

  1. extractionThe product was extracted with ether (2×)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e709e164a3f445faa4c0d5baa480df4d
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613942B1

Verknüpfte Notizen

Wird geladen…