Sulfuric Acid → 7-Chloro-2-nitrosonaphthalen-1-ol

HRID 1287582Notes

Reaction equation

HRID 1287582 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[OH:14])=[CH:6][CH:5]=1.[N:15]([O-])=[O:16].[Na+].S(=O)(=O)(O)O>O>[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([N:15]=[O:16])=[C:11]2[OH:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 132157107-Chloronaphthalen-1-olHCID 23668193Sodium Nitrite

Product 1

HCID 215053107-Chloro-2-nitrosonaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide, 22.4 g in 1.0 liter of water, is added 100 g (0.56 mole) of the chloronaphthol (V). The mixture is stirred with slight heating until solution is complete. The solution is then cooled to -5° to 0° and treated with sodium nitrite, 40.0 g, (0.6 mole) followed by the addition of concentrated sulfuric acid (176 ml) over a 90-minute period. Ice-water (600 ml) is added periodically to prevent clumping of the solid which forms. When addition of the acid is complete, the reaction mixture is stirred for another hour at -5° to 0°. The product is filtered, washed with 4.0 liters of cold water, air-dried overnight and then dried in vacuum oven at 60° for 2.5 days. Yield: 108.6 g (93.4%) light yellow-green solid.

Workup

  1. temperaturewith slight heating until solution
  2. temperatureThe solution is then cooled to -5° to 0°
  3. additionWhen addition of the acid
  4. stirringthe reaction mixture is stirred for another hour at -5° to 0°
  5. filtrationThe product is filtered
  6. washwashed with 4.0 liters of cold water
  7. customair-dried overnight
  8. customdried in vacuum oven at 60° for 2.5 days

Sources & evidence

ORD record
ord-5be75bb54e0340c89acf77c053508e57
Source dataset
uspto-grants-1976_10
Patent number
US03985731

Reaction notes

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