Methylparaben → Methyl 4-(4-phenylbutoxy)benzoate

HRID 52607

Reaktionsgleichung

Reaktionsgleichung von HRID 52607
[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-].[Na+].[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>CN(C=O)C>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 7456MethylparabenHCID 14798Sodium HydroxideHCID 2596681-Bromo-4-phenylbutaneHCID 10942334Sodium Methoxide

Produkt 1

HCID 10978973Methyl 4-(4-phenylbutoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of methyl 4-hydroxybenzoate (13.4 kg, 88 mol) in DMF (52 L) was added dropwise to a mixture of NaOMe (4.8 kg, 89 mol) and DMF (50 L) at room temperature under a gentle stream of nitrogen. The reaction mixture was heated at 60°-70° for 1 hr with stirring and then cooled to room temperature. To this mixture was added dropwise a solution of 4-phenylbutyl bromide (16.92 kg, 79.4 mol) in DMF (5 L). The resulting mixture was heated at 60°-70° for 1 hr with constant stirring and cooled to room temperature. After an addition of 1N-NaOH (110 L) was added, and the product was extracted twice with ethyl acetate (50 L and 80 L). The extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively, and then concentrated to dryness in vacuo to give the title compound in quantitative yield.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 60°-70° for 1 hr
  2. temperatureThe resulting mixture was heated at 60°-70° for 1 hr
  3. stirringwith constant stirring
  4. temperaturecooled to room temperature
  5. additionwas added
  6. extractionthe product was extracted twice with ethyl acetate (50 L and 80 L)
  7. washThe extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively
  8. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1459c7ee68434c8ab950324f3d1949b0
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616721

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