Hydrochloric Acid → HCID 178458861, compound

HRID 978997Notes

Reaction equation

HRID 978997 reaction equation
Cl.C([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH:17]2[CH2:22][C:21](=[O:23])[C:20]([C:24](=[O:27])[CH2:25][CH3:26])=[C:19]([OH:28])[CH2:18]2)=[C:12]([CH3:29])[CH:11]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH3:16][C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([CH3:29])[C:13]=1[CH:17]1[CH2:18][C:19](=[O:28])[C:20]([C:24](=[O:27])[CH2:25][CH3:26])=[C:21]([OH:23])[CH2:22]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178458862HCID 178458862, compound

Product 1

HCID 178458861HCID 178458861, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a535900747344eba8fac1bda2017e66e
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

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