Hydrochloric Acid → 2,3-Dihydroxy-1-naphthaldehyde

HRID 1583766Notes

Reaction equation

HRID 1583766 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Cl-].[K+].Cl.C[CH2:17][O:18]CC>[C-]#N.[Zn+2].[C-]#N>[OH:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 4873Potassium ChlorideHCID 70912,3-Dihydroxynaphthalene

Product 1

HCID 133438102,3-Dihydroxy-1-naphthaldehydeYield 85.7%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

120 g of 2,3-dihydroxynaphthalene, 132 g of ZN(CN)2 (zinc cyanide) and 1.32 g of potassium chloride in 1200 ml of absolute ether were placed in a 2.5 l sulfonation flask equipped with inlet-tube, stirrer, thermometer, reflux condenser and calcium chloride tube. Hydrogen chloride gas was introduced for 6 hours while cooling with ice and stirring. Subsequently, the ether was decanted and destroyed with sodium hydroxide. In order to remove the residual ether, the oily residue was evacuated hot, then treated with 800 ml of water and stirred at 60° C. on a steam-bath. The cooled mixture was filtered under suction and the material on the suction filter was dried at 40° C. in vacuo. The crude product was dissolved in acetonitrile while warming, filtered and, after concentration in vacuo, crystallized. There were obtained 121.3 g (85.7% of theory) of 2,3-dihydroxy-naphthaldehyde of melting point 132°-133° C.

Workup

  1. customequipped with inlet-tube, stirrer
  2. temperaturethermometer, reflux condenser and calcium chloride tube
  3. temperaturewhile cooling with ice
  4. customSubsequently, the ether was decanted
  5. customdestroyed with sodium hydroxide
  6. customIn order to remove the residual ether
  7. customthe oily residue was evacuated hot
  8. additiontreated with 800 ml of water
  9. stirringstirred at 60° C. on a steam-bath
  10. filtrationThe cooled mixture was filtered under suction
  11. filtrationthe material on the suction filter
  12. customwas dried at 40° C. in vacuo
  13. dissolutionThe crude product was dissolved in acetonitrile
  14. temperaturewhile warming
  15. filtrationfiltered
  16. concentrationafter concentration in vacuo
  17. customcrystallized

Sources & evidence

ORD record
ord-ddae1e4c91d64cf0b42c929db47ebc86
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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