Nitric Acid → 5-Methoxy-2-nitrophenol

HRID 512439

Reaction equation

HRID 512439 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[N:10]([O-:12])=[O:11].[Na+].[N+]([O-])(O)=O>C(O)(=O)CC.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[C:5]([OH:9])[CH:4]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 90073-MethoxyphenolHCID 23668193Sodium Nitrite

Product 1

HCID 2196355-Methoxy-2-nitrophenolYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1032Propionic AcidSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 3-methoxyphenol (10 g, 80.55 mmol) in propionic acid (80 mL) was treated at −5° C. with a solution of NaNO2 (5.61 g, 81.30 mmol) in water (13 mL). After stirring for 1 h at −5° C., nitric acid (6.7 mL, 161.10 mmol) was added. The slurry was stirred for 1 h at −5° C., and then at room temperature for 16 h. Water (80 mL) was then added in a dropwise fashion at room temperature. The resultant solid was filtered, washed with 50% aqueous propionic acid, and dried to give 7.47 g (55%) of 5-methoxy-2-nitro-phenol.

Workup

  1. stirringThe slurry was stirred for 1 h at −5° C.
  2. waitat room temperature for 16 h
  3. filtrationThe resultant solid was filtered
  4. washwashed with 50% aqueous propionic acid
  5. customdried

Sources & evidence

ORD record
ord-2c4cde720fbb48ae9f7069f409d00640
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Linked notes

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