Hydrochloric Acid → 1-Hydroxynaphthalene-7-sulfonic acid

HRID 528801

Reaction equation

HRID 528801 reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[OH:16]S([O-])=O.[Na+].[OH-].[Na+].Cl>O>[OH:16][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8386Cleve's acidHCID 14798Sodium HydroxideHCID 23665763Sodium Bisulfite

Product 1

HCID 30224821-Hydroxynaphthalene-7-sulfonic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-amino-2-naphthalenesulfonic acid (Aldrich, 2.40 g, 10.8 mmol) and 3.9M aq. NaHSO3 solution (20.0 mL, 77.0 mmol) in water (10.0 mL) was refluxed for 15 h. The reaction mixture was then basified with 30% aq. NaOH solution (430 mg, 10.8 mmol) and refluxed for 4 h. The reaction mixture was neutralized with conc. HCl and then concentrated in vacuo. The remaining solid was azeotroped with 1:1 MeOH/PhMe (3×) to give the title compound (2.41 g, 95%). 1H NMR (DMSO-d6) δ 9.43 (br s, 1H), 8.36 (s, 1H), 7.96 d, J=8.4 Hz, 1H), 7.88-7.78 (m, 2H), 7.52 (t, J=7.8 Hz, 1H), 7.43 (d, J=7.3 Hz, 1H); MS(ESI−) m/z 222.3 (M−H)−.

Workup

  1. temperaturerefluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe remaining solid was azeotroped with 1:1 MeOH/PhMe (3×)

Sources & evidence

ORD record
ord-38d8d658b8c0402f91d2326e7952801e
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Linked notes

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