Methyl 5-chloro-2-methoxybenzoate → (5-Chloro-2-methoxyphenyl)methanol

HRID 488754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488754
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH3:12])=[C:4]([CH2:3][OH:2])[CH:9]=1

Komponenten

4

Edukt 2

HCID 118574Methyl 5-chloro-2-methoxybenzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 4357585(5-Chloro-2-methoxyphenyl)methanolAusbeute 999,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-chloro-2-methoxy-benzoic acid methyl ester (20 g, 9.97 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of lithium aluminum hydride (210 mL, 210 mmol, 1M soln. in THF). The solution was then warmed to reflux for 2 hours. The reaction was cooled to 0° C. and carefully quenched by the addition of cold water. The mixture was filtered through celite and the filter cake was washed with diethyl ether. The filtrate was washed with saturated aqueous sodium hydrogen carbonate then dried over magnesium sulfate. Concentration in vacuo gave the title compound (17.2 g).

Aufarbeitung

  1. temperatureThe solution was then warmed
  2. temperatureto reflux for 2 hours
  3. customcarefully quenched by the addition of cold water
  4. filtrationThe mixture was filtered through celite
  5. washthe filter cake was washed with diethyl ether
  6. washThe filtrate was washed with saturated aqueous sodium hydrogen carbonate
  7. dry with materialthen dried over magnesium sulfate
  8. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-104b59a1c9ec4ba28783cf03d48e3895
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974817B2

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