Hydrochloric Acid → 2-(2-Hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol

HRID 31314

Reaktionsgleichung

Reaktionsgleichung von HRID 31314
[SH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[C:16]1([CH:22]2[CH2:24][O:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O>[OH:23][CH2:24][CH:22]([S:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7276Styrene OxideHCID 11430Potassium CarbonateHCID 27361672-Mercaptobenzene-1,4-diol

Produkt 1

HCID 179785022-(2-Hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-mercaptobenzene-1,4-diol (0.5 g) and potassium carbonate (0.49 g) in water (5 ml) was added 2-phenyloxirane (0.40 ml) under argon. The mixture was stirred at room temperature for 2.5 hours and then treated with 2 M HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried and evaporated. The crude product was purified by column chromatography using heptane-ethyl acetate (1:1) as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 8.94 (br s, 1H), 8.72 (br s, 1H), 7.24-7.37 (m, 5H), 6.62-6.65 (m, 2H), 6.47 (dd, 1H, J 8.6, 2.8 Hz), 4.97 (br s, 1H), 4.34 (m, 1H), 3.72 (m, 2H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-64fdd82e7fb34dfcb404b245e8d54464
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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