4-Carboxychalcone → HCID 22251491, compound

HRID 1923465Notes

Reaction equation

HRID 1923465 reaction equation
[O:1]=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1>[Ni].C(O)C>[O:1]=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 39957814-Carboxychalcone

Product 1

HCID 22251491HCID 22251491, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4-(3-Oxo-3-phenyl-propenyl)-benzoic acid (7.64 g, 30 mmol) is combined with Raney nickel (2 g) in ethanol (140 mL). The mixture is hydrogenated at room temperature and 50 psi for 1.5 h. The reaction is filtered evaporated in vacuo. The resulting residue is recrystallized from ethyl acetate to obtain 4.57 g (59%) of the titled compound. m.p.=145-147° C.; Anal. Calcd for C16H14O3: C, 75.58; H, 5.55. Found: C, 75.60; H, 5.32.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe reaction is filtered
  3. customevaporated in vacuo
  4. customThe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d8ef56805cad48769ca5617b918e30b8
Source dataset
uspto-grants-2012_05
Patent number
US08178528B2

Reaction notes

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