Nitric Acid → 3-Ethoxy-4-hydroxy-5-nitro-benzoic acid methyl ester

HRID 1990860Notes

Reaction equation

HRID 1990860 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1.[N+:15]([O-])([OH:17])=[O:16]>C(OCC)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:15]([O-:17])=[O:16])[C:7]([OH:10])=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18701970HCID 18701970, compound

Product 1

HCID 686988033-Ethoxy-4-hydroxy-5-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-ethoxy-4-hydroxy-benzoic acid methyl ester (5.3 g, 27.0 mmol, 1.0 equiv) in diethyl ether (60 mL) was added dropwise nitric acid 65% (3.71 mL, 5.24 g, 54.0 mmol, 2.0 equiv) over a period of 30 min. After the addition was completed the reaction mixture was stirred for 4 h at rt. The reaction product precipitated out of solution, was filtered off, washed with cold diethyl ether (3×20 mL) and dried yielding 4.61 g (%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.53 (t, J=7.0 Hz, 3H), 3.94 (s, 3H), 4.21 (q, J=7.0 Hz, 2H), 7.75 (d, J=1.8 Hz, 1H), 8.42 (d, J=1.8 Hz, 1H), 11.01 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.56, 52.59, 65.77, 118.37, 118.54, 121.36, 133.59, 149.44, 149.83, 165.09. MS (ISN): 240.1 [M−H]−.

Workup

  1. additionAfter the addition
  2. customThe reaction product precipitated out of solution
  3. filtrationwas filtered off
  4. washwashed with cold diethyl ether (3×20 mL)
  5. customdried

Sources & evidence

ORD record
ord-54f37f68983b4f298302e80ca518ee97
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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