Potassium Carbonate → Methyl 2-(5-chloro-2-formylphenoxy)propionate

HRID 482390

Reaktionsgleichung

Reaktionsgleichung von HRID 482390
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[CH:8][CH:9]=1)[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH:3]=1)[O:10][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 5201014-Chloro-2-hydroxybenzaldehyde

Produkt 1

HCID 53800060Methyl 2-(5-chloro-2-formylphenoxy)propionateAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 22.0 g (0.141 mole) of 4-chlorosalicylaldehyde, 30 g (0.22 mole) of anhydrous potassium carbonate, and 30.0 g (0.184 mole) of methyl 2-bromopropionate in 120 mL of N,N-dimethylformamide was heated at 80° C. for approximately 17 hours. At the end of that period, the reaction mixture was poured over ice and extracted successively with diethyl ether and ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and filtered. The solvents were then evaporated under reduced pressure, leaving a residue weighing 20 g. This residue was purified by placing it on a silica gel column and eluting with diethyl ether/petroleum ether (25/75). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 6.23 g of methyl 2-(5-chloro-2-formylphenoxy)propionate was isolated as a yellow liquid. Similarly, other fractions were combined and evaporated, yielding 1.69 g of methyl 2-(3-chloro-2-formylphenoxy)propionate as a yellow liquid. The NMR spectra of both compounds were consistent with proposed structure of each. This reaction was repeated several times.

Aufarbeitung

  1. additionAt the end of that period, the reaction mixture was poured over ice
  2. extractionextracted successively with diethyl ether and ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvents were then evaporated under reduced pressure
  7. customleaving a residue
  8. customThis residue was purified
  9. washeluting with diethyl ether/petroleum ether (25/75)
  10. customthe solvents evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-77556498ad65497299a03aa6cd1ad8b6
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05798316

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