4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid → 4-[3-(Methyloxy)-3-oxopropyl]-1-naphthalenecarboxylic acid

HRID 1669735Notes

Reaction equation

HRID 1669735 reaction equation
[CH3:1][O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 673480204-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid2×

Product 1

HCID 673464244-[3-(Methyloxy)-3-oxopropyl]-1-naphthalenecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid (for example as prepared for Intermediate 5) (1.73 g, 5.09 mmol) is hydrogenated over palladium on carbon (10 wt %, 350 mg) in ethanol (50 ml) for 4 h. The catalyst is removed by filtration through Celite, and the mixture hydrogenated again with fresh catalyst (350 mg) overnight. The mixture is filtered through Celite and concentrated to afford the title compound.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customhydrogenated again with fresh catalyst (350 mg) overnight
  3. filtrationThe mixture is filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-161b37ffdded43908f00f8765328aabd
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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