4-Formylbenzoic acid → Methyl 4-Formylbenzoate

HRID 887

Reaktionsgleichung

Reaktionsgleichung von HRID 887
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:12][Si](C=[N+]=[N-])(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:12][O:2][C:1](=[O:3])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 120884-Formylbenzoic acidHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 15294Methyl 4-Formylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 9.6 g (63.6 mmol) of 4-carboxybenzaldehyde (Aldrich Chemical Co.) in 100 mL of CH2Cl2 at 0° C. was added excess trimethylsilyldiazomethane and the resulting mixture was allowed to stir at 0° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to give 4.3 g of the ester 167 as an oil. 1H NMR consistent with the product.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dec073da1f4d41b387cb25d85d14d5f1
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723459

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