Reaktion #1063248

Reaktionsgleichung

HCl

4-methylthiobenzyl bromide

thiotetronic acid

potassium hydroxide

→

solid

Ausbeute 26.5%

4-Hydroxy-3-[[4-(methylthio)phenyl]methyl]-2(5H)-thiophenone

Ausbeute 26.5%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONpoured into H20
2. 2
   Extraktionextracted with EtOAc
3. 3
   TrocknenThe organic extracts were dried over MgSO4
4. 4
   SonstigeEvaporation and purification by flash chromatography on acid
5. 5
   Waschenwashed (5% H3PO4 in MeOH) silica gel (eluting solvent hexane/EtOAc 1/3)

Vorschrift

To a suspension of 4-methylthiobenzyl bromide (5.6 g. 25.8 mmol), thiotetronic acid (3.0 g, 25.8 mmol) in dioxane (50 ml), was added aqueous potassium hydroxide (25.8 mL). The mixture was stirred at temperatures in the range of 65°-70° C. for 3 hours. Then, the mixture was cooled to room temperature, poured into H20, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acid washed (5% H3PO4 in MeOH) silica gel (eluting solvent hexane/EtOAc 1/3) gave a white solid (1.72 g, 26.5%): m.p. 206°-208° C.

Quelle