Benzaldehyde → 6254-48-4

HRID 364694Notes

Reaction equation

HRID 364694 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[CH:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>O.[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C1(C)C=CC=CC=1>[C:9]1([CH:8]([OH:15])[C@@H:2]([C:3]([OH:5])=[O:4])[NH2:1])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium Hydroxide

Product 1

HCID 123141536254-48-4Yield 86.5%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Glycine (60 g) and 48 g of sodium hydroxide were dissolved in 500 g of water. Then, 0.5 g of trioctylmethyl ammonium chloride was added, and with stirring at 25° to 30° C., a solution of 169.6 g of benzaldehyde in 150 g of toluene was added dropwise over the course of about 1 hour. The reaction was further carried out at 25° to 35° C. for 20 hours. After the reaction, 209 g of 35% hydrochloric acid was added dropwise at a temperature of less than 40° C. The mixture was stirred at room temperature for 1 hour. After standing, the lower aqueous layer was separated, neutralized with 45% sodium hydroxide to a pH of 6 at room temperature, stirred at 0° to 5° C. for 1 hour, filtered, washed with cold water, and dried to give 125.3 g of β-phenylserine. The purity of the product was 90.6%. The yield based on glycine was 78.3%.

Workup

  1. additionwas added dropwise at a temperature of less than 40° C
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customthe lower aqueous layer was separated
  4. customneutralized with 45% sodium hydroxide to a pH of 6 at room temperature
  5. stirringstirred at 0° to 5° C. for 1 hour
  6. filtrationfiltered
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-46dbdb980cd54ddfbb538839fe051534
Source dataset
uspto-grants-1986_08
Patent number
US04605759

Reaction notes

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