Methanol → E-5-Decen-1-ol

HRID 1416986

Reaktionsgleichung

Reaktionsgleichung von HRID 1416986
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])(=O)C.CO.[OH-].[Na+]>CCCCCC>[CH2:5]([OH:4])[CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 38027Dec-5-enyl acetate

Produkt 1

HCID 92458E-5-Decen-1-olAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A portion of the acetate is removed and converted to the corresponding alcohol as follows. 15.0 g (67 mmol) of the 5-decenyl acetate, 35 mL of methanol and 34 mL of 2 M sodium hydroxide were added to a 250 mL round-bottomed flask. This mixture was stirred for 3 hours at room temperature. After 3 hours the hydrolysis was complete, 10 mL of hexane was added and the solution was washed with 10 mL of 1 M HCl, 10 mL of NaHCO3 -saturated water and 10 mL of brine. The organic phase was dried with sodium sulfate, filtered and the hexane removed under reduced pressure to yield 9.4 g of 5-decenol. GC analysis showed the isometric ratio to be 80:20 E:Z.

Aufarbeitung

  1. customA portion of the acetate is removed
  2. waitAfter 3 hours the hydrolysis was complete
  3. washthe solution was washed with 10 mL of 1 M HCl, 10 mL of NaHCO3 -saturated water and 10 mL of brine
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe hexane removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a6bfda5146ce4928a76fc0c336283733
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916983

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