Nitric Acid → HCID 59361944, compound

HRID 1808523Notes

Reaction equation

HRID 1808523 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[O:8])=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][O:19][CH3:20].[N+:21]([O-])([OH:23])=[O:22]>CC(O)=O>[CH3:1][O:2][C:3]1[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[O:8])=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 59361929HCID 59361929, compound

Product 1

HCID 59361944HCID 59361944, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-methoxyethyl 4-methoxy-3-(2-methoxyethoxy)benzoate (15.05 g, 52.9 mmol) in AcOH (54 mL) under an atmosphere of N2 was added conc. HNO3 (13.5 mL) in one portion. The reaction was stirred at RT for 72 h. The mixture was poured into ice-water (ca. 800 mL) and extracted with EtOAc (2×400 mL). The combined organics were washed with water (2×200 mL) and brine (1×200 mL), dried (Na2SO4) and conc. in vacuo. The residue was azeotroped with heptane (2×300 mL) to remove residual AcOH giving 2-methoxyethyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate as a dark colored oil. (15.5 g, 47.1 mmol, 89%). HPLC retention time 6.24 mins.

Workup

  1. extractionextracted with EtOAc (2×400 mL)
  2. washThe combined organics were washed with water (2×200 mL) and brine (1×200 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe residue was azeotroped with heptane (2×300 mL)
  5. customto remove residual AcOH

Sources & evidence

ORD record
ord-611343843e2a4100ad9cda3103fe2247
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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