2,7-Naphthalenediol → HCID 13750455, compound

HRID 1613118Notes

Reaction equation

HRID 1613118 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH:3]=1.[N:13]([O-])=[O:14].[Na+]>C(O)(=O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[N:13]=[O:14]

Participants

4

Reactant 2

HCID 113972,7-NaphthalenediolHCID 23668193Sodium Nitrite2×

Product 1

HCID 13750455HCID 13750455, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,7-Dihydroxynaphthalene (BAYER) (250 g=1.56 mol) was dissolved in 875 ml of glacial acetic acid at 0°-90° C. and precipitated again by addition of 2.5 kg of crushed ice. A very finely disperse, light-beige, viscous suspension was formed and the temperature fell to -10° to -12° C. With good stirring and external cooling, 107.88 g (1.56 mol) of solid sodium nitrite were introduced in portions into this suspension, the mixture was stirred for another hour and a further 10.7 g (0.56 mol) of solid sodium nitrite were then added. Stirring was then continued for a further two hours at -8° to -5° C. The 2,7-dihydroxy-1-nitrosonaphthalene formed as dark-red crystals was filtered off with suction and well-pressed on the suction filter. The reaction product, still moist from the suction filter, was then stirred into 5 1 of water at 20°-25° C. for about one hour, again filtered off with suction, pressed down well and dried for 24 hours at 20°-25° C. in a circulating-air oven.

Workup

  1. customprecipitated again by addition of 2.5 kg of crushed ice
  2. additionA very finely disperse
  3. customlight-beige, viscous suspension was formed
  4. customfell to -10° to -12° C
  5. stirringthe mixture was stirred for another hour
  6. stirringStirring

Sources & evidence

ORD record
ord-3a819b7e394842b0abfb8cdcb3cb805c
Source dataset
uspto-grants-1993_03
Patent number
US05192640

Reaction notes

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