Water → 4-(1-Propoxyethyl)benzoic acid

HRID 1354794

Reaktionsgleichung

Reaktionsgleichung von HRID 1354794
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1)[CH3:3].[CH2:14](I)[CH2:15][CH3:16].[H-].[Na+].O>CN(C=O)C>[CH2:14]([O:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3])[CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Produkt 1

HCID 144734334-(1-Propoxyethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 4-(1-hydroxyethyl)benzoate (2.0 g) dissolved in DMF (30 ml) was mixed with propyl iodide (3.8 g), and then sodium hydride (50% in oil, 0.53 g) was added. After the end of the exothermic reaction, the mixture was stirred for 1 hour and then water was cautiously added. It was extracted with ethyl acetate, and the organic phase was dried over sodium sulfate, filtered and concentrated. The residue was hydrolyzed by method P-a. This resulted in the product with the molecular weight of 208.26 (C12H16O3); MS (ESI): 209 (M+H+).

Aufarbeitung

  1. customAfter the end of the exothermic reaction
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis resulted in the product with the molecular weight of 208.26 (C12H16O3)

Quellen und Nachweise

ORD-Eintrag
ord-26726afcdd094cd9880a8a290125792b
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223788B2

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