Reaction #64060

Reaction equation

hydrochloric acid

5-(4-benzyloxy-2,6-dimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one

→

5-(2,6-dimethyl-4-hydroxyphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one

Yield 100.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Washwashed with water
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherEvaporation of the solvent

Procedure

Palladium on activated carbon (0.30 g), followed by concentrated hydrochloric acid (20 ml), were added to a solution of 5-(4-benzyloxy-2,6-dimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (see Example 36) (3.22 g; 8.5 mmole) in ethyl acetate (200 ml). The mixture was hydrogenated at atmospheric pressure for 3 hours, then filtered, washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 5-(2,6-dimethyl-4-hydroxyphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (2.45 g; 100%) as a yellow oil.

Source