Dimethyl Sulfoxide → Anisole, m-pentadecyl-

HRID 2099911

Reaktionsgleichung

Reaktionsgleichung von HRID 2099911
CS(C)=O.[CH2:5]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].[CH3:29]I>O>[CH2:5]([C:20]1[CH:21]=[C:22]([O:26][CH3:29])[CH:23]=[CH:24][CH:25]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 68146Hydrogenated cardanol

Produkt 1

HCID 578947Anisole, m-pentadecyl-Ausbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 2-liter round-bottomed flask was placed 500 milliliters (ml) of dimethyl sulfoxide, 100 grams (g) of 3-(n-pentadecyl)phenol (0.33 mol), and 73.55 g of potassium hydroxide (1.31 mol). To this mixture, 93.5 g of methyl iodide (0.66 mol) was added drop wise with stirring at room temperature. After the addition, the reaction mixture was stirred for a further 6 hours. Then the reaction mixture was poured into deionized water (1.5 liters). The organic material was extracted by addition of diethyl ether. The diethyl ether layer was separated, washed with water, dried over anhydrous sodium sulfate, and finally evaporated to afford the crude product as a viscous fluid. This material was purified by silica gel column chromatography using petroleum ether as the eluent to furnish 3-(n-pentadecyl)anisole (104.6 g, 97% of theoretical yield) having a melting range of 27-28° C.

Aufarbeitung

  1. customInto a 2-liter round-bottomed flask was placed
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for a further 6 hours
  4. extractionThe organic material was extracted by addition of diethyl ether
  5. customThe diethyl ether layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customfinally evaporated
  9. customto afford the crude product as a viscous fluid
  10. customThis material was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fdf3f431d5264fa4b53618d7beaf2a73
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569714B2

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