Dichloromethane → 9-Tetradecen-1-ol, acetate

HRID 638393

Reaktionsgleichung

Reaktionsgleichung von HRID 638393
[CH:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:16]([OH:30])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH3:29].ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CCCCCC>[CH:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:1]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:15])[CH3:2]

Komponenten

7

Edukt 4

HCID 6344Dichloromethane2×HCID 37064Tetradec-9-en-1-olHCID 620729-TetradecenalHCID 178418287HCID 178418287, Verbindung

Produkt 2

HCID 280169-Tetradecen-1-ol, acetateAusbeute 36 %HCID 620729-Tetradecenal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained.

Aufarbeitung

  1. customprepared in the same manner
  2. filtrationthe mixture was filtered
  3. customThe solvent was evaporated
  4. distillationthe product vacuum distilled through a 2 ft.×3/4 in

Quellen und Nachweise

ORD-Eintrag
ord-15213315cdd642e3beb096e340f51c27
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560792

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