Reaktion #955900

Reaktionsgleichung

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

Ausbeute 72.0%

Lösungsmittel

dimethylformamide

—

ice water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (DCM) (3×50 ml)
2. 2
   TrocknenThe organic part was dried by MgSO4
3. 3
   Sonstigesolvent was removed under a rotary evaporator
4. 4
   SonstigeThe crude product was purified on silica gel column

Vorschrift

(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).

Quelle