Ethylparaben → 4-[4-[(3-Ethyl-3-oxetanyl)methoxy]butoxy]benzoic acid

HRID 7330

Reaktionsgleichung

Reaktionsgleichung von HRID 7330
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]1([CH2:24][CH3:25])[CH2:23][O:22][CH2:21]1>CN(C)C=O>[CH2:24]([C:20]1([CH2:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=2)[CH2:21][O:22][CH2:23]1)[CH3:25]

Komponenten

4

Edukt 2

HCID 8434EthylparabenHCID 219893153-[(4-Bromobutoxy)methyl]-3-ethyloxetane

Produkt 1

HCID 219606284-[4-[(3-Ethyl-3-oxetanyl)methoxy]butoxy]benzoic acidAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 300 ml three neck flask, 5.2 g (31 mmol) of ethyl p-hydroxybenzoate, 4.7 g (34 mmol) of potassium carbonate anhydride, and 7.8 g (31 mmol) of the 3-[(4-bromobutoxy)methyl]-3-ethyloxetane were dissolved in 50 ml of dimethylformamide. After the solution remained turbid was heated to a temperature of 80° C. and stirred for 4 hours, the solvent was completely distilled out in a vacuum. To the resulting yellow oily substance were added 15 ml of a 7% sodium hydroxide aqueous solution and 15 ml of methanol. The mixture was refluxed for two and half hours. 1 N (normality) of hydrochloric acid was added to the mixture such that the pH is adjusted to about 3. The resulting white precipitate was filtered and dried in a vacuum thereby obtaining 8.6 g (28 mmol) of 4-[7-(3-ethyl-3-oxetanyl)-1,6-dioxaheptyl]benzoic acid (yield: 89%, identified with 1H-NMR). The resulting compound was no more purified and used in the following reaction.

Aufarbeitung

  1. distillationthe solvent was completely distilled out in a vacuum
  2. additionTo the resulting yellow oily substance were added 15 ml of a 7% sodium hydroxide aqueous solution and 15 ml of methanol
  3. temperatureThe mixture was refluxed for two and half hours
  4. addition1 N (normality) of hydrochloric acid was added to the mixture such that the pH
  5. filtrationThe resulting white precipitate was filtered
  6. customdried in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e20a963324004b499bf87587735aa884
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087273B2

Verknüpfte Notizen

Wird geladen…