O-Cresol → ((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrile

HRID 408672

Reaktionsgleichung

Reaktionsgleichung von HRID 408672
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S-:9][C:10]#[N:11].[Na+].[Na+].[Br-].BrBr.C([O-])(O)=O.[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([S:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[OH:8]

Komponenten

7

Edukt 5

HCID 335O-CresolHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 220928((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrileAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a 250 ml flask were added 10.8 g o-methylphenol, 26.0 g sodium thiocyanate, 70 ml methanol, added dropwise 100 ml methanol solution containing 10.3 g NaBr, 5.3 ml liquid bromine at 0° C. under N2 atmosphere. The mixture was stirred at room temperature for 3 hours. The mixture was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2 for four times. The extract was dried over anhydrous Na2SO4, filtrated, evaporated and purified by column chromatograph (petroleum ether:ethyl acetate=8:1) to obtain 11.1 g yellow solid, yield 67.27%. 1H-NMR (400 MHz, CDCl3, δ ppm) δ 2.2558 (3H, s), 5.0 (1H, s), 6.8 (1H, d, J=8.4 Hz), 7.3605-7.2631 (1H, m), 7.3542 (1H, s).

Aufarbeitung

  1. extractionextracted with CH2Cl2 for four times
  2. dry with materialThe extract was dried over anhydrous Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. custompurified by column chromatograph (petroleum ether:ethyl acetate=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-33b17429b9824748931f65f162f6d6d6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759355B2

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