Reaction #42526

Reaction equation

O(Et)2

methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate

BF3

→

methyl 3-butyryl-4-hydroxybenzoate

Solvents

benzene

Conditions

Workup

1. 1
   Otherquenched with saturated sodium bicarbonate
2. 2
   Extractionfollowed by extraction with dichloromethane
3. 3
   DryingThe organic layer was dried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

To a stirred solution of methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate in benzene was added BF3.O(Et)2 (1.3 mL, 10 mmol). The mixture was stirred for 0.25 h and then quenched with saturated sodium bicarbonate followed by extraction with dichloromethane. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford methyl 3-butyryl-4-hydroxybenzoate which was used without further purification or characterization.

Source