HCID 14028056, compound → HCID 66981029, compound

HRID 876200Notes

Reaction equation

HRID 876200 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.C(OCC)(=O)C.[Pd]>[CH:1]1([CH2:6][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 2

HCID 14028056HCID 14028056, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66981029HCID 66981029, compoundYield 98.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of cyclopentyl(3,4-dimethoxyphenyl)methanone (10.8 g, 0.046 mol), wet Pd/C (1 g) in 10 ml of acetic acid and 10 ml of ethyl acetate was put in an autoclave at 60° C. with 20 bars of hydrogen during 24 hours. Filtration over Celite® and concentration gave 10 g of pale brown oil. This oil was purified by vacuum distillation (100-120° C., 0.02 mbar) through a short path to give 7.1 g (70%) of a colorless liquid.

Workup

  1. filtrationFiltration
  2. concentrationover Celite® and concentration

Sources & evidence

ORD record
ord-b413d66e85b944fa904b60111be3f250
Source dataset
uspto-grants-2015_03
Patent number
US08987188B2

Reaction notes

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