Reaktion #1747831

Reaktionsgleichung

dichloromethane

hydrochloride

3-aminophenylacetic acid

thionyl chloride

ethanol

→

desired compound

Ausbeute 100.0%

3-aminophenylacetic acid ethyl ester

Ausbeute 100.0%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto slowly rise to rt
2. 2
   SonstigeEvaporation of the volatiles
3. 3
   Sonstigegave a beige solid
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto remove diethyl sulphite
6. 6
   SonstigeRecrystallization from dietyl ether

Vorschrift

To a cooled solution (−15° C.) of 3-aminophenylacetic acid (10.2, 67 mmol) in ethanol (200 mL) was added dropwise thionyl chloride (10 mL, 0.14 mol). The reaction mixture was stirred for 24 h allowing the temperature to slowly rise to rt. Evaporation of the volatiles gave a beige solid that was stripped several times with dichloromethane. The solid was then treated with hot diethyl ether and filtered to remove diethyl sulphite. Recrystallization from dietyl ether gave 14.4 g, 67 mmol, 100% of the desired compound as an off-white crystalline hydrochloride, mp 135° C. IR (KBr) cm−1 2857,2614, 1740

Quelle