Reaction #955900

Reaction equation

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

Yield 72.0%

Solvents

dimethylformamide

—

ice water

Conditions

Workup

1. 1
   Extractionextracted with dichloromethane (DCM) (3×50 ml)
2. 2
   DryingThe organic part was dried by MgSO4
3. 3
   Othersolvent was removed under a rotary evaporator
4. 4
   OtherThe crude product was purified on silica gel column

Procedure

(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).

Source