Malonic Acid → 3-Amino-3-(4-methylphenyl)propanoic acid

HRID 745248Notes

Reaction equation

HRID 745248 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 77254-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27336803-Amino-3-(4-methylphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 10 ml of p-tolualdehyde, were added 180 ml of ethanol, 9.8 g of malonic acid, and 15.8 g of ammonium acetate. The mixture was refluxed for 5 hours. After cooling, the insolubles were removed by filtration. After addition of 100 ml of water, the filtrate was adjusted to pH 7.0 with 1N hydrochloric acid, and the precipitated crystals were collected by filtration to yield 5.4 g of β-amino-β-(4-methylphenyl)propionic acid; m.p. 228°-229° C.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe insolubles were removed by filtration
  4. additionAfter addition of 100 ml of water
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-75f73cb4a52a49e8913c11d472063eb0
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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