Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Glycine | HCID 750 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Catalyst | Trioctylmethylammonium chloride | HCID 21218 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 6254-48-4 | HCID 12314153 | 86.5% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04605759 |
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| Source dataset | uspto-grants-1986_08 |
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| ORD ID | ord-46dbdb980cd54ddfbb538839fe051534 |
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| Source note | uspto-grants-1986_08 |
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