Hydrochloric Acid → 3-Chloro-2-hydroxybenzaldehyde

HRID 1739492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739492
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].Cl>COCCOCCOC>[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]=[O:6]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 30225173-Chloro-2-hydroxybenzoyl chlorideHCID 16684435Lithium tritertbutoxyaluminohydride

Produkt 1

HCID 5196513-Chloro-2-hydroxybenzaldehydeAusbeute 14,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

3-Chloro-2-hydroxybenzoylchloride (8.7 mmol) was dissolved in diglyme (10 ml) and cooled to -70° C. under argon. Lithium tritertbutoxyaluminohydride (0.5M, 34.8 ml 17.4 mmol) was added via syringe keeping the temperature below -60° C. The reaction was stirred at -60° C. for 2% hours. The reaction mixture was poured onto ice, acidified with concentrated HCl and extracted with ethyl acetate (2×). The organic phases were combined, dried over MgSO4 and evaporated. Flash chromatography (eluant: CH2Cl2 /hexanes) gave the title product (0.2 g, 1.3 mmol). MS (CI+) (M+NH4)+ 174

Aufarbeitung

  1. customthe temperature below -60° C
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fbc4e3a475b04882a81d9f2edec511a5
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965741

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