Potassium Hydroxide → 4-Octyloxy-2-(pent-4-en-1-yloxy)benzoic acid

HRID 2220008

Reaktionsgleichung

Reaktionsgleichung von HRID 2220008
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][C:5]=1[O:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24].[OH-].[K+]>C1COCC1.O>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[C:5]([O:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])[CH:6]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 69309676Methyl 4-(octyloxy)-2-[(pent-4-en-1-yl)oxy]benzoate

Produkt 1

HCID 179809634-Octyloxy-2-(pent-4-en-1-yloxy)benzoic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

77.5 g (0.22 mol) of 4-Octyloxy-2-(pent-4-en-1-yloxy)benzoic acid methyl ester obtained in Step 2 is dissolved in 700 mL of THF. A solution of 66.6 (1.19 mol) of KOH in 200 mL of water is added. The mixture is heated to reflux and stirred for 6 h. The mixture is allowed to return to room temperature, then the solvents are distilled off and ice/water is added. After acidification with concentrated HCl, the mixture is extracted with several times with CH2Cl2. The resulting organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The product recrystallised from hexane gives a pure product as white crystals (66.9 g, 92%).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customto return to room temperature
  4. distillationthe solvents are distilled off
  5. additionice/water is added
  6. extractionAfter acidification with concentrated HCl, the mixture is extracted with several times with CH2Cl2
  7. dry with materialThe resulting organic phase is dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe product recrystallised from hexane

Quellen und Nachweise

ORD-Eintrag
ord-36524391ca4641a2b0573ade8e43bc35
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07416682B2

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