2-Bromoethanol → 4-((2-Hydroxyethyl)thio)phenol

HRID 330712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330712
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][OH:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[OH:12][CH2:11][CH2:10][S:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Produkt 1

HCID 130526324-((2-Hydroxyethyl)thio)phenolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(FIG. 2) (a) (4-(2-hydroxyethylsulfanyl) phenol) was synthesized by a modified literature procedure (pl add ref). 4-hydroxythiophenol (mercaptophenol) (6.00 g, 47.61 mmole), 2-bromoethanol (5.90 g, 47.6 mmol) and K2CO3 (6.6 g, 47.48 mmol) was stirred in dimethylformamide (DMF, 50 ml) at −5° C. for 30 minutes. The reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was poured in ice water (300 ml) and extracted with dichloromethane (DCM) (3×50 ml). The organic part was dried by MgSO4 and then solvent was removed under a rotary evaporator. The crude product was purified on silica gel column by using a chloroform/methanol (94:6) solvent mixture. Yield: 72%. 1H NMR (CDCl3): δ, 8.01 (s, OH, 1H), 7.33 (d, 2H, J=8.7 Hz), 6.78 (d, 2H, J=8.7 Hz), 4.52 (s, OH, 1H), 3.67 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=5.7).

Aufarbeitung

  1. extractionextracted with dichloromethane (DCM) (3×50 ml)
  2. dry with materialThe organic part was dried by MgSO4
  3. customsolvent was removed under a rotary evaporator
  4. customThe crude product was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-a342cb291e2d42a7b6819310f85c9b58
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08876914B2

Notizen zur Reaktion

Wird geladen…