Sulfuric Acid → 3-Hydroxy-4-(methoxycarbonyl)benzoic acid

HRID 2103808Notes

Reaction equation

HRID 2103808 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].N([O-])=[O:16].[Na+].S(=O)(=O)(O)O>Cl.C(O)(=O)C>[OH:16][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 670501783-Hydroxy-4-(methoxycarbonyl)benzoic acidYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To 3-amino-4-methoxycarbonylbenzoic acid (1.95 g, 10 mmol) suspended in 3 M hydrochloric acid (12.5 mL) and acetic acid (20 mL), an aqueous solution (20 mL) of sodium nitrite (0.69 g, 10 mmol) was added at −10° C., and the resulting solution was stirred for 30 minutes. The solution was added to 10% aqueous sulfuric acid (30 mL) at 0° C., and the resulting reaction mixture was heated with reflux for 1 hour. The desired product was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and purified by silica gel column chromatography to give 1.04 g of the desired product as a white solid (yield 53%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperaturewith reflux for 1 hour
  4. extractionThe desired product was extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-1abfb2ad3ace4d42a22d9ecef366eb3c
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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