Benzaldehyde → DL-beta-Phenylalanine

HRID 1018177Notes

Reaction equation

HRID 1018177 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([OH:15])(=[O:14])[CH2:10]C(O)=O.C([O-])(=O)C.[NH4+:20]>C(O)C>[C:2]1([CH:1]([CH2:10][C:9]([OH:15])=[O:14])[NH2:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 867Malonic AcidHCID 517165Ammonium Acetate

Product 1

HCID 69189DL-beta-PhenylalanineYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 270 mL of ethanol were added 115 g (1.08 mol) of benzaldehyde, 113 g (1.08 mol) of malonic acid, and 167 g (2.16 mol) of ammonium acetate, followed by stirring for 5 hours under heating and refluxing. Precipitated white crystals were filtered and the filtrate was recrystallized from a water-ethanol mixed solvent (1:4, 2.5 L), to give 85.14 g of the title compound (II) as white crystals (yield 48%).

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. customPrecipitated white crystals
  4. filtrationwere filtered
  5. customthe filtrate was recrystallized from a water-ethanol mixed solvent (1:4, 2.5 L)

Sources & evidence

ORD record
ord-ca3534aee764445895781407ca1317fc
Source dataset
uspto-grants-2002_11
Patent number
US06479702B1

Reaction notes

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