Nitric Acid → HCID 20064141, compound

HRID 1360289Notes

Reaction equation

HRID 1360289 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-054cdceb02cc43d289e713b0401da750
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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