Resorcinol → HCID 178514110, compound

HRID 436881Notes

Reaction equation

HRID 436881 reaction equation
[N:1]#[C:2]Cl.[C:4]1([CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)[OH:5].C([N:14](CC)CC)C>C(O)(C)C>[O-:5][C:2]#[N:1].[O-:8][C:7]#[N:14].[C:4]1([CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)[OH:5]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 8471TriethylamineHCID 10477Cyanogen Chloride

Product 1

HCID 178514110HCID 178514110, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 271 g (4.4 mols) of cyanogen chloride in 1.1 liter of isopropanol is introduced at 0° to -5° C. into a 3 liter glass vessel equipped with a stirrer and a thermometer. By means of a metering pump, a solution of 220 g (2 mols) of resorcinol and 420 g (4.04 mols) of triethyl amine in 750 ml of isopropanol is introduced with stirring through an inlet pipe projecting below the surface. The pumping rate is adjusted in such a way that the reaction temperature can be kept at -5° C. to +3° C. On completion of the reaction, the crystalline sludge formed is filtered off under suction from the isopropanol. The filter residue is thoroughly stirred with 1.1 liter of water and filtered off under suction again. The residue thus obtained is then thoroughly washed with water and dried in a stream of air at 25° to 30° C. 276 g (86% of the theoretical) of resorcinol dicyanate are obtained in this way. Mp: 81° C., nD90 :1.4980

Workup

  1. customequipped with a stirrer
  2. customcan be kept at -5° C. to +3° C
  3. customOn completion of the reaction
  4. customthe crystalline sludge formed
  5. filtrationis filtered off under suction from the isopropanol
  6. stirringThe filter residue is thoroughly stirred with 1.1 liter of water
  7. filtrationfiltered off under suction again
  8. customThe residue thus obtained
  9. washis then thoroughly washed with water
  10. customdried in a stream of air at 25° to 30° C

Sources & evidence

ORD record
ord-85e20e89602743e29c29b92a21f41567
Source dataset
uspto-grants-1977_06
Patent number
US04028393

Reaction notes

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