Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 363036

Reaktionsgleichung

Reaktionsgleichung von HRID 363036
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH:19]=[CH2:18]

Komponenten

5

Edukt 3

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 10796Cesium carbonate

Produkt 1

HCID 4645407Methyl 4-(allyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 4-hydroxybenzoate (22-1) (9.72 g, 64.36 mmol) in 100 mL of DMF was added 24.8 g (76.0 mmol) of Cs2CO3 followed by 5.0 mL (58.5 mmol) of allyl bromide. The resulting solution was then heated at 50° C. for 5 h. The solvent was distilled under reduced pressure and the residue was taken up in 200 mL of EtOAc. The organic phase was extracted with 1N NaOH (2×50 mL), water (5×50 mL) and brine (50 mL), dried (MgSO4) and concentrated to afford product 22-2 as a white solid.

Aufarbeitung

  1. distillationThe solvent was distilled under reduced pressure
  2. extractionThe organic phase was extracted with 1N NaOH (2×50 mL), water (5×50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0bb51fc263f846a8968028086a25ac20
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872138

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