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Dimethylformamide → Benzeneacetic acid, 4-(dodecyloxy)-

HRID 2165333
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2165333
[CH3:1]N(C)C=O.CC[C:8]1[CH:13]=[C:12](O)[CH:11]=[CH:10][C:9]=1[O:15][C:16]([CH3:18])=O.C(Br)C[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:32](=[O:35])([O-])[O-:33].[K+].[K+]>O>[CH2:16]([O:15][C:9]1[CH:8]=[CH:13][C:12]([CH2:1][C:32]([OH:33])=[O:35])=[CH:11][CH:10]=1)[CH2:18][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 46173007HCID 46173007, Verbindung

Produkt 1

HCID 10336152Benzeneacetic acid, 4-(dodecyloxy)-Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a dimethylformamide (DMF, 100 ml) solution of ethyl 4-hydroxyphenyl acetate (18 g, 0.1 mol.) and dodecyl bromide (25 g, 0.1 mol.) was added potassium carbonate (15 g, 0.1 mol.). The mixture was stirred at 100° C. for one hour. To the reaction solution, after cooling, was added water (200 ml), which was subjected to extraction with isopropyl ether (IPE). The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml). To the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.), and the mixture was stirred at 50° C. The reaction solution was concentrated under reduced pressure, and the pH was adjusted to 4, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure to leave crude crystals Recrystallization from hexane-IPE gave 4-dodecyloxyphenylacetic acid (1-e, 20 g, 63%).

Aufarbeitung

  1. temperatureTo the reaction solution, after cooling
  2. extractionwas subjected to extraction with isopropyl ether (IPE)
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml)
  7. additionTo the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.)
  8. stirringthe mixture was stirred at 50° C
  9. concentrationThe reaction solution was concentrated under reduced pressure
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customto leave crude
  15. customcrystals Recrystallization from hexane-IPE

Quellen und Nachweise

ORD-Eintrag
ord-558d21888ece4ddfa2b6bc46ff6f12ce
Quelldatensatz
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04939274

Notizen zur Reaktion

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