Sodium Hydroxide → 3-(3-methoxy-4-methylphenyl)propanoic acid

HRID 1859806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859806
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:6][CH:7](C(OC)=O)[C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH:16]=[CH:17][C:18]=1[CH3:19]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 18626507HCID 18626507, Verbindung

Produkt 1

HCID 31636013-(3-methoxy-4-methylphenyl)propanoic acidAusbeute 123 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 25.84 g (0.1072 mol) of dimethyl 2-(3-methoxy-4-methylbenzyl)malonate in 150 mL of MeOH was treated with a solution of 20 g (0.5 mol) of NaOH in 100 mL of H2O and heated at reflux overnight. The solution was concentrated under reduced pressure and the residue taken up in H2O and washed with Et2O. The solution was acidified to Congo Red end point with dilute HCl and the solution extracted with Et2O. The Et2O was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure gave 25.6 g of an oil. This was taken up in 125 mL of dioxane and heated at reflux overnight. Removal of the solvent under reduced pressure gave 20.5 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98/2) gave 8.65 g (41.6% yield) of the product as a white solid, mp 80-82° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 195 (M+H+).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe solution was concentrated under reduced pressure
  4. washwashed with Et2O
  5. extractionthe solution extracted with Et2O
  6. washThe Et2O was washed with saturated NaCl
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f31edde82dad4ca1bc8eca6d1248d2d3
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528535B2

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