6-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one → 6-(3-Hydroxyphenyl)-1-naphthol

HRID 1035650Notes

Reaction equation

HRID 1035650 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[CH:6][CH:7]=1>CC1C=CC(C(C)C)=CC=1.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([OH:18])=[CH:13][CH:12]=[CH:11]3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 114704386-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one

Product 1

HCID 114477036-(3-Hydroxyphenyl)-1-naphtholYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

6-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one (503 mg, 2.11 mmol, 1 eq) and Pd/C (505 mg) are suspended in p-cymene (15 ml). The reaction mixture is refluxed for 6 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/ethyl acetate 9/1 as the eluent yields the desired product in a yield of 16%, 83 mg.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 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/ethyl acetate 9/1 as the eluent

Sources & evidence

ORD record
ord-f42b0548b9a84c2e8582f1e13468dd56
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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