Methyl formate → Methyl 3-hydroxy-2-(3'-phenylphenoxy)propenate

HRID 1381461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381461
[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1.[CH:19](OC)=[O:20].[H-].[Na+]>CN(C=O)C>[OH:20][CH:19]=[C:4]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:18]

Komponenten

5

Edukt 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 13787157Methyl(3-phenylphenoxy)acetate

Produkt 1

HCID 67855452Methyl 3-hydroxy-2-(3'-phenylphenoxy)propenateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Methyl(3-phenylphenoxy)acetate (6.0 g) and methyl formate (30.2 ml) were dissolved in DMF and added dropwise with stirring to a suspension of sodium hydride (1.44 g, 50% dispersion in oil) in DMF at 0° C. (ice-bath). After 45 minutes, the ice-bath was removed and the reaction mixture was stirred for 2 hours at room temperature. Aqueous sodium carbonate was then added. The aqueous layer was washed with ether, acidified to pH 4-5 with concentrated hydrochloric acid and then re-extracted with ether. The combined organic layers were washed with brine, dried, filtered and evaporated to give methyl 3-hydroxy-2-(3'-phenylphenoxy)propenate as a pale yellow oil (6.05 g, 90% yield).

Aufarbeitung

  1. additionadded dropwise
  2. customthe ice-bath was removed
  3. additionAqueous sodium carbonate was then added
  4. washThe aqueous layer was washed with ether
  5. extractionre-extracted with ether
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2c29df9cd2bf446f8e601824b8ff4038
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04802913

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