Hydrochloric Acid → 4-Hydroxy-3-nitrobenzoic acid

HRID 1763057Notes

Reaction equation

HRID 1763057 reaction equation
[OH-:1].[Na+].Cl.Cl[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]>O>[OH:1][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73204-Chloro-3-nitrobenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 120334-Hydroxy-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 5-liter, 3-necked, round-bottom flask is added 532 g of NaOH in 3 liters of water and 520 g of 4-chloro-3-nitrobenzoic acid. The solution is heated to reflux (100° C.) under nitrogen and stirred for 10 hours. Upon completion, the reaction is cooled to room temperature and neutralized with concentrated hydrochloric acid. The product is isolated by filtration, washed with 3 liters of cold water and dried in a vacuum oven at 30° C. overnight at 3 mm Hg. The yield is 430 g (90 percent) of 4-hydroxy-3-nitrobenzoic acid with a melting point of 182° C.-183° C.

Workup

  1. temperatureThe solution is heated
  2. customThe product is isolated by filtration
  3. washwashed with 3 liters of cold water
  4. customdried in a vacuum oven at 30° C. overnight at 3 mm Hg

Sources & evidence

ORD record
ord-ab4247b4ceeb4d02890e599ba6a9d6be
Source dataset
uspto-grants-1989_05
Patent number
US04835306

Reaction notes

Loading…