Nitric Acid → HCID 20040348, compound

HRID 641323Notes

Reaction equation

HRID 641323 reaction equation
[N+:1]([O-:4])(O)=[O:2].C[O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[CH:9]=1>C(OCC)C>[OH:14][C:11]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:13][C:8]([C:7]([OH:16])=[O:6])=[CH:9][C:10]=1[CH3:15]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Product 1

HCID 20040348HCID 20040348, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

65% aq. nitric acid solution (2.7 mL, 60 mmol) and fuming nitric acid (2.5 mL, 60 mmol) were added at −10° C. to a solution of 4-hydroxy-3-methyl-benzoic acid methyl ester (4.97 g, 29.9 mmol) in diethyl ether (60 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 4-hydroxy-3-methyl-5-nitro-benzoic acid (6.27 g, 99%). Yellow solid, MS (ISP)=210.1 (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-a304a0924f1f4b91931f39784a283906
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

Loading…