Hydrochloric Acid → Hydrochloric Acid

HRID 1283887

Reaction equation

HRID 1283887 reaction equation
C[O:2][C:3]([C@@H:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[ClH:13]>>[CH:9]1[CH:8]=[CH:7][C:6]([C@H:5]([NH2:12])[C:3]([OH:4])=[O:2])=[CH:11][CH:10]=1.[ClH:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1201451Methyl phenylglycinate, L-

Product 2

HCID 313Hydrochloric AcidHCID 99291L-Phenylglycine

Procedure

A solution of methyl L-phenylglycinate (-)-hemitartrate mono-ethanol solvate ([α]D + 62.4°, 36.888 g., 0.102 mole) in 6N-hydrochloric acid (68 ml., 0.408 mole, 4 equiv.) was refluxed for 1 hour 10 minutes and then distilled for 15 minutes. Water (68 ml.) was added and the pH of the warm solution adjusted to 7.0 with ammonium hydroxide solution (0.880, 35 ml.). The mixture was cooled in ice, filtered, and the solid was washed with water (2 × 25 ml.) and ethanol (25 ml.) and dried over phosphorus pentoxide to give L-phenylglycine as white plates (13.406 g., 87%), [α]D21 + 152.1° (c 1.007, 1N-HCl).

Workup

  1. distillationdistilled for 15 minutes
  2. additionWater (68 ml.) was added
  3. temperatureThe mixture was cooled in ice
  4. filtrationfiltered
  5. washthe solid was washed with water (2 × 25 ml.) and ethanol (25 ml.)
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-a0bc9825e8164839830096a5db6176ac
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Linked notes

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