Hydrochloric Acid → (4-Methoxyphenyl)glycolonitrile

HRID 37625

Reaction equation

HRID 37625 reaction equation
[C-]#N.[Na+].[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[O:13])=[CH:10][CH:11]=1.[CH2:14]([N:16](CC)CC)C.Cl>C(O)C>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:13])[C:14]#[N:16])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 36571(4-Methoxyphenyl)glycolonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 49 g (1 mole) of sodium cyanide and 136 g (1 mole) anisaldehyde in ethyl alcohol 800 ml), containing triethylamine (5 mol %, 5.1 g) is added HCl gas (1 mol, 36.5 g) over 30 minutes at 5°-10° C. The resulting slurry is stirred at that temperature for 6 hours. In situ sampling of the reaction mixture shows the reaction to be complete. Additional HCl (0.2 moles) is added to quench the reaction. tHE solution is filtered and used in the next step without further purification. Yield, ca. 80%.

Workup

  1. aliquotIn situ sampling of the reaction mixture
  2. customthe reaction
  3. customto quench
  4. customthe reaction
  5. filtrationtHE solution is filtered
  6. customused in the next step without further purification
  7. customYield

Sources & evidence

ORD record
ord-d70c30dd3e6440eaa4466dd6b2a1c444
Source dataset
uspto-grants-1995_05
Patent number
US05420349

Linked notes

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