Reaction #742251

Reaction equation

3-(2-hydroxy-phenyl)-acrylic acid ethyl ester

potassium hydroxide

→

colourless crystals

Yield 51.9%

(E)-3-(2-Hydroxy-phenyl)-acrylic acid

Yield 51.9%

Solvents

ethanol

water

Conditions

Workup

1. 1
   Temperatureat reflux for 28 hours
2. 2
   Concentrationthe reaction mixture was concentrated
3. 3
   workup.ADDITIONThe residue was diluted with 500 ml HCl 2N
4. 4
   Extractionextracted with ether
5. 5
   WashThe organic phase was washed with 2N HCl and water
6. 6
   Otherdried
7. 7
   Otherevaporated to dryness
8. 8
   OtherThe resulting solid was recrystallized

Procedure

To a solution of 100.0 g 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester in 500 ml of ethanol, a solution of 50.9 g potassium hydroxide in 500 ml of water was dropped in at room temperature. After stirring at reflux for 28 hours, the reaction mixture was concentrated. The residue was diluted with 500 ml HCl 2N and extracted with ether. The organic phase was washed with 2N HCl and water, dried and evaporated to dryness. The resulting solid was recrystallized to yield 44.3 g of colourless crystals.

Source