1-Acetylnaphthalene → 1-Ethylnaphthalene

HRID 991252Notes

Reaction equation

HRID 991252 reaction equation
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=O.[H][H]>C1C(Cl)=CC=C(Cl)C=1>[CH2:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 136631-Acetylnaphthalene2×HCID 178418361HCID 178418361, compound

Product 1

HCID 143151-EthylnaphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

A 2 mL reactor was charged with 0.150 mL of a 1.00 M solution of 1-acetonaphthalene and 0.050 mL of a 0.030 M solution of [Cp*Ru(CO)2]2(μ-H)}+OTf− in dichlorobenzene. The reaction was heated at 90° C. for 12 hours at 820 psi (5.7 MPa) of hydrogen gas. The reaction was cooled, and analyzed using gas chromatography/mass spectroscopy. Analysis indicated 100% conversion of the 1-acetonaphthalene, with a greater than 90% yield of 1-ethylnaphthalene. Note that in this example, the alcohol itself (presumably initially formed from hydrogenation of the C═O double bond) undergoes a hydrogenation reaction to yield in the final product, 1-ethylnaphthalene.

Workup

  1. temperatureThe reaction was cooled

Sources & evidence

ORD record
ord-92650493635d4362bd11d352349a94f1
Source dataset
uspto-grants-2002_10
Patent number
US06462206B1

Reaction notes

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