HCID 14715596, compound → HCID 24829224, compound

HRID 1035651Notes

Reaction equation

HRID 1035651 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)=[CH:5][CH:4]=1>CC1C=CC(C(C)C)=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([OH:19])=[CH:14][CH:13]=[CH:12]3)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 14715596HCID 14715596, compound

Product 1

HCID 24829224HCID 24829224, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

6-(4-Methoxyphenyl)-3,4-dihydronaphthalene-1(2H)-one (510 mg, 2.02 mmol, 1 eq) and Pd/C (528 mg) are suspended in p-cymene (7 ml). The reaction mixture is refluxed for 24 h, cooled, filtered over Celite and extracted with 1 M NaOH. The aqueous phase is acidified with 1 M HCl and extracted with ether. The combined organic phases are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with dichloromethane/hexane 5/5 as the eluent yields the desired product in a yield of 14%, 69 mg.

Workup

  1. temperatureThe reaction mixture is refluxed for 24 h
  2. temperaturecooled
  3. filtrationfiltered over Celite
  4. extractionextracted with 1 M NaOH
  5. extractionextracted with ether
  6. washThe combined organic phases are washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum on a rotary evaporator
  10. customPurification by column chromatography with dichloromethane/hexane 5/5 as the eluent

Sources & evidence

ORD record
ord-8747a1a00c314fd2830c03cdc2c9efa4
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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