Methanol → 2-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

HRID 1095948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095948
CO[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Cl:13].[H-].[CH2:16]([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[CH:4]([CH3:16])[CH:3]=[O:14]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 15576550Methyl 2-(2-chloro-5-methoxyphenyl)acetateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 574499712-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-Chloro-5-methoxy-benzeneacetic acid methyl ester (850 mg) was dissolved in toluene (40 mL) and cooled to −78° C. Diisobutylaluminium hydride (20% in toluene, 3.69 mL) was added over a period of 15 minutes. Stirring was continued for 45 minutes at −78° C. Methanol (2 mL) was added followed by 1M potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to r.t. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The title compound was obtained as a light yellow oil (710mg, 96%) and was used without further purification. 1H-NMR (δ, CDCl3): 9.72 (s, 1H), 7.34 (d, 1H), 6.79 (dd, 1H), 6.66 (d, 1H), 4.10 (q, 1H), 3.79 (s, 3H), 1.43 (d, 3H).

Aufarbeitung

  1. customThe cooling bath was removed
  2. temperatureto warm to r.t
  3. additionThe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1246e4b3d1ac42e99aafe7f1c3f03c5e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138189B2

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