Nitric Acid → HCID 20064141, compound

HRID 1660839Notes

Reaction equation

HRID 1660839 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-be6456e633794194a943c59751802aac
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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