Dimethyl Sulfoxide → Anisole, m-pentadecyl-

HRID 2276624

Reaktionsgleichung

Reaktionsgleichung von HRID 2276624
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-].[Na+].[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 14798Sodium HydroxideHCID 68146Hydrogenated cardanol

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a two-liter round bottomed flask was placed dimethyl sulfoxide (500 mL), 3-pentadecyl phenol (100.0 g, 0.33 mol) and sodium hydroxide (73.55 g, 1.31 mol). To this mixture methyl iodide (93.5 g, 0.66 mol) was added drop wise with stirring at room temperature. After the addition, the reaction mixture was stirred for further 6 h. 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 liquid. This material was purified by silica gel column chromatography using petroleum ether as the eluent to obtain 3-pentadecyl anisole Yield 104.6 g (97%), MP 27-28° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fc03ed5376cc44338cd3c06eb9cfab3a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133089B2

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