Dl-Phenylalanine → (-)-Mandelic acid

HRID 1719796Notes

Reaction equation

HRID 1719796 reaction equation
[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.[C:13]([OH:23])(=[O:22])[C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15]>C(O)(=O)C>[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:13]([OH:23])(=[O:22])[C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15]

Participants

5

Reactant 2

HCID 994Dl-PhenylalanineHCID 11914(-)-Mandelic acid

Product 2

HCID 11914(-)-Mandelic acidHCID 71567D-Phenylalanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a vessel, were added 34.24 g of DL-phenylalanine, 47.31 g of D-mandelic acid and 174.2 g of an aqueous 50% acetic acid solution (the total weight of 255.75 g) while stirring. The resultant mixture was heated to form a solution. The solution was slowly cooled to 25° C. for 3 hours and then, was stirred at the same temperature for 2 hours. As a result, a complex of D-phenylalanine and D-mandelic acid was crystallized and the crystals were collected by filtration, were washed with 10 ml of water and were dried. A crude complex of D-phenylalanine and D-mandelic acid having [α]D20 of -56.50° (c=2, in H2O) and an optical purity of 91.0% was obtained in yield of 25.59 g.

Workup

  1. customto form a solution
  2. stirringwas stirred at the same temperature for 2 hours
  3. customAs a result, a complex of D-phenylalanine and D-mandelic acid was crystallized
  4. filtrationthe crystals were collected by filtration
  5. washwere washed with 10 ml of water
  6. customwere dried

Sources & evidence

ORD record
ord-90de4bdfd427440abe8438ff2326da85
Source dataset
uspto-grants-1985_09
Patent number
US04542236

Reaction notes

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