Potassium Cyanide → HCID 15572607, compound

HRID 903951Notes

Reaction equation

HRID 903951 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:7]=[O:8].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[C-:28]#[N:29].[K+]>COCCOCCOC.O.C(O)C>[OH:8][CH:7]([CH:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[O:5][C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[O:2][CH3:1])[C:28]#[N:29]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 656671Sodium PyrosulfiteHCID 54397602HCID 54397602, compound

Product 1

HCID 15572607HCID 15572607, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8150DiglymeSolvent

Procedure

150 g of α-(2-methoxy-phenoxy)-phenyl acetaldehyde dissolved in approximately 1800 ml of diglyme was stirred with 176.5 g of sodium metabisulphite in 550 ml of water and 200 ml of ethanol at 50° C. for 16 hours. The whole was cooled to room temperature and addition was made of 44.4 g of potassium cyanide in 200 ml of water. The whole was stirred at 90° C. (external temperature) for 5 hours, concentrated to approximately 800 ml and poured into water: extraction was performed with 4×750 ml of ethyl ether and the whole washed with water, dried over Na2SO4 and evaporated to dryness to obtain 156.5 g of 2-hydroxy-3-phenyl-3-(2-methoxy-phenoxy)-propionitrile as a viscous oil. Yield=94%. Analogously, all the 2-hydrox-propionitrile derivatives useful for the preparation of the 2-hydroxy-propylamines mentioned in Examples 3 and 4 were prepared.

Workup

  1. additionaddition
  2. concentrationconcentrated to approximately 800 ml
  3. additionpoured into water
  4. extractionextraction
  5. washthe whole washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-27fef0dfe157428fa3e02423cc8b2ec5
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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