Nitric Acid → HCID 20064141, compound

HRID 641320Notes

Reaction equation

HRID 641320 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Cl:15])[CH:9]=1>C(OCC)C>[CH3:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([N+:1]([O-:4])=[O:2])[C:11]([OH:14])=[C:10]([Cl:15])[CH:9]=1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 20064141HCID 20064141, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

65% aq. nitric acid solution (2.4 mL, 54 mmol) and fuming nitric acid (2.2 mL, 54 mmol) were added at −10° C. to a solution of 3-chloro-4-hydroxy-benzoic acid methyl ester (5.00 g, 26.8 mmol) in diethyl ether (65 mL). The ice bath was removed and the reaction mixture was stirred at room temperature for 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to afford 3-chloro-4-hydroxy-5-nitro-benzoic acid methyl ester (6.24 g, 100%). Yellow solid, MS (ISP)=230.3 (M−H)−.

Workup

  1. customThe ice bath was removed
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d26bf5b780e44e1f844b22c0204f3041
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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