Butanal → Dl-Phenylalanine

HRID 435465Notes

Reaction equation

HRID 435465 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=O)CC.C(=O)CCC>CO>[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 261ButanalHCID 1032Propionic AcidHCID 6140L-Phenylalanine

Product 1

HCID 994Dl-PhenylalanineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

3 g of L-phenylalanine, 90 ml of 80% propionic acid and 0.3 ml (0.2 mole per mole of L-phenylalanine) of n-butyraldehyde were admixed. The mixture was stirred at 100° C. for 3 hours. After the reaction, the mixture was condensed to dryness, and 10 ml of methanol were added to the residue. The methanolic mixture was ice-cooled, and the crystalline precipitates were collected by filtration. 2.70 g of DL-phenylalanine were thereby obtained.

Workup

  1. customAfter the reaction
  2. additionwere added to the residue
  3. temperaturecooled
  4. customthe crystalline precipitates
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-6c3d1aa908c043538a3bc1348e2f0e9a
Source dataset
uspto-grants-1983_08
Patent number
US04401820

Reaction notes

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