Benzaldehyde → 2-Propenoic acid, 3-phenyl-

HRID 381533Notes

Reaction equation

HRID 381533 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O-:12])(=[O:11])[CH3:10].[NH4+].C(O)(=O)CC(O)=O>C(O)C>[C:9]([OH:12])(=[O:11])[CH:10]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 867Malonic AcidHCID 517165Ammonium Acetate

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

β-substituted-β-amino-acids were prepared by refluxing the corresponding benzaldehyde derivatives with excess ammonium acetate (˜2 equiv.), and malonic acid (1 equiv.) in absolute ethanol until the reaction has completed (determined by TLC and NMR). Cinnamic acid derivative was produced as a side product. The reaction mixtures were then workup with standard procedures, e.g., as described in FIG. 4.

Sources & evidence

ORD record
ord-45eabb32aac44d68a60760d30ceb4ac8
Source dataset
uspto-grants-2001_10
Patent number
US06306909B1

Reaction notes

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