Salicylaldehyde → 2-Phenylglycine

HRID 435464

Reaction equation

HRID 435464 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C(=O)[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15]>C(O)(=O)C>[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:6]=1.[CH:17]1[C:18]([CH:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:19][CH:13]=[C:14]([OH:15])[CH:16]=1

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 99291L-Phenylglycine

Product 2

HCID 38662-PhenylglycineHCID 921434-Hydroxyphenylglycine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

6 g of L-phenylglycine or L-p-hydroxyphenylglycine were suspended in a mixture of 20 ml of 95% acetic acid and 0.2 ml (0.05 mole per mole of the L-amino acid used) of salicylaldehyde. The suspension was stirred at 100° C. for 2 hours. After the reaction, the mixture was cooled to room temperature, and the crystalline precipitates were collected by filtration and then washed with methanol. DL-phenylglycine or DL-p-hydroxyphenylglycine was thereby obtained. The results are shown in Table 17.

Workup

  1. customAfter the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. customthe crystalline precipitates
  4. filtrationwere collected by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-f17dfdb554054d039e49e8fe4c287923
Source dataset
uspto-grants-1983_08
Patent number
US04401820

Linked notes

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