Methylparaben → Methyl 4-(4-chlorobutoxy)benzoate

HRID 1709849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1709849
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutane

Produkt 1

HCID 14575308Methyl 4-(4-chlorobutoxy)benzoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 30.4 g (0.2 mole) of methyl-4-hydroxybenzoate, 68.6 g (0.4 mole) of 1-bromo-4-chlorobutane and 82.9 g (0.6 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 17 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to give an oil which crystallized. The solid was triturated with cold petroleum ether (30°-60° C.), collected by filtration, and dried to yield 44.3 g (92%) of title compound as a white solid. An analytical sample, mp 28.5°-29° C., was prepared from petroleum ether (30°-60° C.).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 17 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give an oil which
  7. customcrystallized
  8. customThe solid was triturated with cold petroleum ether (30°-60° C.)
  9. filtrationcollected by filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-68c69c2b47884835a5ac936eac489027
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04950674

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