Reaction #2210

Reaction equation

hydrochloric acid

aluminum trichloride

naphthalene

succinic anhydride

→

3-(1-naphthoyl)propionic acid

Solvents

nitrobenzene

Conditions

Workup

1. 1
   workup.ADDITIONwas added to a well
2. 2
   workup.STIRRINGThe resulting mixture was stirred overnight at room temperature
3. 3
   workup.ADDITIONThe mixture was then poured slowly onto ice-water (600 g)
4. 4
   FiltrationThe crude acid was filtered
5. 5
   Washwashed with water until washings
6. 6
   Otherrecrystallized from ethanol yielding the product (m.p. 170°-172° C.)

Procedure

A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid. The crude acid was filtered, washed with water until washings were neutral and recrystallized from ethanol yielding the product (m.p. 170°-172° C.).

Source