Ammonium Chloride → (2-Benzyloxyphenyl)-(4-methylsulfanyl-phenyl)methanol

HRID 554527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554527
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]([C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)[OH:22])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 3447842-(Benzyloxy)benzaldehydeHCID 178503242HCID 178503242, Verbindung

Produkt 1

HCID 67459728(2-Benzyloxyphenyl)-(4-methylsulfanyl-phenyl)methanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a nitrogen stream, a solution of 4-methylsulfanyl-phenylmagnesium bromide in THF (0.5 M, 35 mL) was added dropwise to a solution of 2-benzyloxybenzaldehyde (2.60 g, 12.2 mmol) in THF (24 mL) at 0° C. and the mixture was stirred at room temperature for two hours, and then a saturated ammonium chloride aqueous solution was added thereto under cooling with ice and the mixture was extracted with ethyl acetate. 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 (1:4)] to obtain the title compound (3.91 g, 95%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e56e184b5ef54d4f90254602f3a895b4
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048897B2

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