2-Nitroso-1-naphthol → 2-(Chloroformyl)-cis-cinnamonitrile

HRID 1287578

Reaction equation

HRID 1287578 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[N:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[OH:19])=O>CCCCCC>[Cl:2][C:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1/[CH:17]=[CH:18]\[C:9]#[N:7])=[O:19]

Participants

4

Reactant 2

HCID 85922-Nitroso-1-naphtholHCID 24819Phosphorus pentachloride

Product 1

HCID 124488532-(Chloroformyl)-cis-cinnamonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a rapidly stirring suspension of phosphorus pentachloride (197.5 g) in dry hexane (3.5 liters) is added 167.0 g (0.964 mole) of 2-nitroso-1-naphthol. The mixture is stirred at room temperature for 1 hour after which it is refluxed for 1 hour, cooled slightly and decanted while hot. The residue is boiled with hexane (3.0 liters) for another hour after which the solution is decanted and combined with the first hexane extract. It is evaporated down to dryness. Yield: 200.0 g (crude). This residue is extracted with hexane (2.0 liters), the hexane decanted, cooled, and the resultant crystals are filtered off. The filtrate is used to reestract additional compound from the above residue (the reextraction being repeated four times) with cooling and filtering of the crystals obtained each time. Yield: 79.0 g (42.5%), mp=72°-74°.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour after which it
  2. temperatureis refluxed for 1 hour
  3. temperaturecooled slightly
  4. customdecanted while hot
  5. waitThe residue is boiled with hexane (3.0 liters) for another hour
  6. customafter which the solution is decanted
  7. extractionextract
  8. customIt is evaporated down to dryness
  9. extractionThis residue is extracted with hexane (2.0 liters)
  10. customthe hexane decanted
  11. temperaturecooled
  12. filtrationthe resultant crystals are filtered off
  13. temperaturewith cooling
  14. filtrationfiltering of the crystals
  15. customobtained each time

Sources & evidence

ORD record
ord-2ccce5b6b95b432bacc83489aeb5669d
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Linked notes

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