Nitric Acid → Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate

HRID 631266Notes

Reaction equation

HRID 631266 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][Cl:13])=[C:6]([O:14][CH3:15])[CH:5]=1.C(OC(=O)C)(=O)C.[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:10][CH2:11][CH2:12][Cl:13])=[CH:8][C:9]=1[N+:24]([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 230330164-(2-Chloro-ethoxy)-5-methoxy-benzoic acid methyl ester

Product 1

HCID 23032998Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

The intermediate 4-(2-chloro-ethoxy)-3-methoxy-benzoic acid methyl ester (2.7 g, 11.03 mmol) was taken in acetic acid (30 mL) and acetic anhydride (6 mL) was added. The solution was cooled to 0° C. and 90% nitric acid (2 mL) was added. The reaction mixture was stirred for 10-15 minutes at ambient temperature, then heated to 50° C. for 2h. Completion of the reaction was monitored by TLC. The reaction mixture was cooled and was poured on to crushed ice. The precipitate formed was filtered and was dried to afford the pure 4-(2-chloro-ethoxy)-5-methoxy-2-nitro-benzoic acid methyl ester (2.73 g, 85%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.35 (s, 1H), 4.42 (t, 2H), 4.10-3.90 (m, 5H), 3.80 (m, 3H).

Workup

  1. temperatureheated to 50° C. for 2h
  2. temperatureThe reaction mixture was cooled
  3. additionwas poured on
  4. customto crushed ice
  5. customThe precipitate formed
  6. filtrationwas filtered
  7. customwas dried

Sources & evidence

ORD record
ord-e601c8c16f0a49a5b83edb6e54eefbea
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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