Naphthalen-1(2H)-one → 2-Benzyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1953400Notes

Reaction equation

HRID 1953400 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:6]([CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[C:5]1[CH:10]=[CH:1][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 12446728Naphthalen-1(2H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 5635332-Benzyl-1,2,3,4-tetrahydronaphthalen-1-oneYield 114.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A Parr® hydrogenation bottle was charged with naphthalen-1-one (15 gm), ethyl acetate (150 mL) and 1 g of 10% palladium on charcoal. The mixture was hydrogenated on a Parr® shaker for about 15 hrs under 20 psi of hydrogen. The resulting mixture was filtered through a pad of Celite® and concentrated in vacuo to afford a red oil which was purified by flash chromatography (3:1 hexane/diethyl ether) to afford 14.1 gm of benzyltetralone, mp 50-51° C. Analysis calculated for C18H18O2 : 266.1302. Found: 266.1308.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. customto afford a red oil which
  4. customwas purified by flash chromatography (3:1 hexane/diethyl ether)

Sources & evidence

ORD record
ord-cf2e5b91e47c427c875fbafba4b30fc4
Source dataset
uspto-grants-2000_09
Patent number
US06117874

Reaction notes

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