Acetic Acid → 5-[(1,5-Dimethylhexyl)oxy]pentanal

HRID 414896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414896
[CH3:1][CH:2]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1OCC[O:15]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].C(O)(=O)C.O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][CH:2]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 66623666{4-[(1,5-Dimethylhexyl)oxy]butyl}-1,3-dioxolane

Produkt 1

HCID 866420235-[(1,5-Dimethylhexyl)oxy]pentanalAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

{4-[(1,5-dimethylhexyl)oxy]butyl}-1,3-dioxolane (1.4 g, 43% pure by GC RPA, 3.9 mmol), acetic acid (10 mL), tetrahydrofuran (16 mL) and water (20 mL) were added to a 100 mL three-necked flask fitted with thermocouple, magnetic stirrer and condenser. The reaction mixture was refluxed for 2 hrs, cooled and saturated sodium carbonate (150 mL) added. The crude reaction mixture was extracted with hexane (4×100 mL), the combined organic phase dried over magnesium sulphate, filtered and the solvent removed in vacuo. The crude product was chromatographed over silica gel (hexane/methyltert-butyl ether) to yield pure 5-[(1,5-dimethylhexyl)oxy]pentanal as a colourless oil (0.22 g, 1.02 mmol, chemical yield 26%).

Aufarbeitung

  1. customfitted with thermocouple, magnetic stirrer and condenser
  2. temperatureThe reaction mixture was refluxed for 2 hrs
  3. temperaturecooled
  4. customThe crude reaction mixture
  5. extractionwas extracted with hexane (4×100 mL)
  6. dry with materialthe combined organic phase dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe crude product was chromatographed over silica gel (hexane/methyltert-butyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-a124b7fabb02462cb655ee245bf1f3b1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088725B2

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