Sodium Hydroxide → 5-Hydroxy-2-nitrobenzoic acid

HRID 1672321Notes

Reaction equation

HRID 1672321 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-:14].[Na+]>>[OH:14][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 118825-Hydroxy-2-nitrobenzoic acid

Procedure

124.6 g (0.618 mol) of 5-chloro-2-nitro-benzoic acid (Fluka Buchs, Switzerland) are heated under reflux in an aqueous sodium hydroxide solution [197.8 g (4.94 mol) of NaOH in 1.23 l water] for 18 h. The cold reaction mixture is extracted several times with ether-ethyl acetate, washed with brine and dried over sodium sulfate. The raw material is crystallized from isopropyl ether-hexane. The crystals are filtered off and dried at 50° C. (high-vacuum). mp: 167-171° C.; MS: 182 (M+−1); HPLC: W-=6.315 min (Grad 1).

Workup

  1. customThe cold reaction mixture
  2. extractionis extracted several times with ether-ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe raw material is crystallized from isopropyl ether-hexane
  6. filtrationThe crystals are filtered off
  7. customdried at 50° C. (high-vacuum)
  8. customW-=6.315 min (Grad 1)

Sources & evidence

ORD record
ord-1dea71d51572457cbe1327ddd9ee4c84
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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