Water → Methyl 3-hydroxy-5-nitrobenzoate

HRID 431384Notes

Reaction equation

HRID 431384 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[C:19]([O-])([O-])=O.[Na+].[Na+].O>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 8203933-Hydroxy-5-nitrobenzoic acid

Product 1

HCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-hydroxy-5-nitrobenzoic acid (2.00 g, 11 mmol) and concentrated sulfuric acid (0.5 mL) in MeOH (15 mL) was refluxed overnight, cooled to room temperature, and poured into mixture of Na2CO3 (saturated solution, 25 mL), water (150 mL), and ice (50 g). Resulting precipitate was filtered, washed with water (3×30 mL), and air-dried. Yellow microcrystals, yield 1.37 g (63%). 1H NMR (DMSO-d6, 400 MHz), δ: 10.94 (s, 1H); 8.09 (s, 1H); 7.78 (s, 1H); 7.71 (s, 1H); 3.90 (s, 3H).

Workup

  1. customResulting precipitate
  2. filtrationwas filtered
  3. washwashed with water (3×30 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-f874f77347bf42398aa8eee6aedda577
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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