Water → 2-(4-Methylsulfanylbenzyl)phenol

HRID 554507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554507
CSC.C([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=1)C1C=CC=CC=1.O>C(Cl)Cl>[CH3:26][S:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[OH:11])=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 674612941-Benzyloxy-(4-methylsulfanylbenzyl)benzene

Produkt 1

HCID 674586422-(4-Methylsulfanylbenzyl)phenolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a nitrogen stream, dimethylsulfide (7.25 mL, 138 mmol) and a boron trifluoride-diethyl ether complex (2.1 mL, 8.8 mmol) were added to a solution of 1-benzyloxy-(4-methylsulfanylbenzyl)benzene (1.9 g, 5.9 mmol) in methylene chloride (15 mL) under cooling with ice, and the reaction mixture was stirred for 48 hours while gradually raising its temperature to room temperature. Water was added thereto under cooling with ice and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (1.19 g, 91%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Quellen und Nachweise

ORD-Eintrag
ord-d15715a9b1184917a01e35f32481ea0b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048897B2

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