Sodium Bicarbonate → 3,4-Dihydroxy-5-nitrobenzoic acid

HRID 1880436Notes

Reaction equation

HRID 1880436 reaction equation
Cl([O-])=O.[Na+].[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14])[CH:9]=[O:10].P([O-])(O)(O)=[O:19].[Na+].C([O-])(O)=O.[Na+]>O.CS(C)=O.O>[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14])[C:9]([OH:19])=[O:10]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 144509823,4-Dihydroxy-5-nitrobenzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

A solution of sodium chlorite (47.6 g, 526 mmol) in water (350 mL) was added dropwise to a solution of 3,4-dihydroxy-5-nitrobenzaldehyde (68.8 g, 376 mmol) and sodium dihydrogen phosphate (45.1 g, 376 mmol) in DMSO/H2O mixture (375 mL/150 mL) at room temperature for 1.5 hours. The reaction mixture was stirred at room temperature for 1 hour and poured into a separatory funnel containing a 5% solution NaHCO3 (500 mL). The product was extracted with dichloromethane (3×100 mL). The water layer was acidified with concentrated HCl to pH˜1 and extracted with ether (3×250 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, and evaporated to afford 3,4-dihydroxy-5-nitrobenzoic acid (70.3 g, 353 mmol, 94% yield).

Workup

  1. additionpoured into a separatory funnel
  2. extractionThe product was extracted with dichloromethane (3×100 mL)
  3. extractionextracted with ether (3×250 mL)
  4. washThe combined organic layers were washed with brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-daedc14e68eb41e38794c0ca7003d099
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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