Sodium Iodide → 2-Methoxy-4-propylphenyl 4-methylbenzenesulfonate

HRID 1023900

Reaktionsgleichung

Reaktionsgleichung von HRID 1023900
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[OH:12].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(#N)C>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][C:4]2[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][CH3:11])=[CH:8][C:3]=2[O:2][CH3:1])(=[O:23])=[O:22])=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 177394-Propylguaiacol

Produkt 1

HCID 591913892-Methoxy-4-propylphenyl 4-methylbenzenesulfonateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-methoxy-4-propylphenol (10.0 mmol; 1.6 mL), NaI (1.0 mmol; 150 mg), and K2CO3 (11.0 mmol; 1.52 g), under argon, in acetonitrile (20 mL) was added tosyl chloride (10.5 mmol; 2.0 g). The reaction mixture was stirred at 70° C. for 36 hr, then quenched with NaOH (0.1N; 3 mL), and extracted with ethyl acetate (2*10 mL). Combined organic phases were washed with saturated NaHCO3 sat. (5 mL), dried over MgSO4, concentrated in vacuo. The crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane) to yield the desired compound as a clear oil (2.13 g; 6.6 mmol; 66%).

Aufarbeitung

  1. customquenched with NaOH (0.1N; 3 mL)
  2. extractionextracted with ethyl acetate (2*10 mL)
  3. washCombined organic phases were washed with saturated NaHCO3 sat. (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-477b4905aaed4a62861d78ee7c90c858
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722746B2

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