The following is the strategy in modern synthesis of indigo dye in industry. A, formaldehyde and hydrogen cyanide converted into N-phenylglycinonitrile at 85 ° Hydrolysis takes place in aqueous alkali at 100 °C. The sodamide for the next stage is obtained by passing ammonia over molten sodium. The dried salt of phenylglycine (B) is dissolved in a eutectic, and therefore stirrable, mixture of sodium and potassium hydroxides at 220 °C and portions of molten sodamide are added. The reaction leads to sodium indoxylate, which undergoes oxidative hydrolysis to give indigo (yield of 84 %). CN NaOH/KOH A+CH₂O + HCN B + NH3 85 °C H₂O 100 °C 2 NaNH. NaOH/KOH 220 °C ONa NNa H₂0.0₂ 80-90 °C

The following is the strategy in modern synthesis of indigo dye in industry. A, formaldehyde and hydrogen cyanide converted into N-phenylglycinonitrile at 85 ° Hydrolysis takes place in aqueous alkali at 100 °C. The sodamide for the next stage is obtained by passing ammonia over molten sodium. The dried salt of phenylglycine (B) is dissolved in a eutectic, and therefore stirrable, mixture of sodium and potassium hydroxides at 220 °C and portions of molten sodamide are added. The reaction leads to sodium indoxylate, which undergoes oxidative hydrolysis to give indigo (yield of 84 %). CN NaOH/KOH A+CH₂O + HCN B + NH3 85 °C H₂O 100 °C 2 NaNH. NaOH/KOH 220 °C ONa NNa H₂0.0₂ 80-90 °C

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.65P

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