Acetic Acid → HCID 66876546, compound

HRID 1917682Notes

Reaction equation

HRID 1917682 reaction equation
C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:19]([O:21][CH3:22])=[O:20].[N+:28]([O-])([OH:30])=[O:29]>O>[Cl:12][CH2:13][CH2:14][O:15][C:16]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([N+:28]([O-:30])=[O:29])=[C:18]([CH:17]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 66876629HCID 66876629, compound

Product 1

HCID 66876546HCID 66876546, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To acetic acid (42 mL) and acetic anhydride (8.5 mL) was added methyl 3-(2-chloroethoxy)-4-methoxybenzoate (4.0 g, 16.3 mmol) followed by 70% nitric acid (2.8 mL) and the mixture heated at 50° C. for 1 hour. The mixture was poured into H2O, filtered, and washed with H2O to give methyl 5-(2-chloroethoxy)-4-methoxy-2-nitrobenzoate (4.08 g, 14.1 mmol, 86%). 1H NMR (300 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.38 (s, 1H), 4.43 (t, 2H), 3.99 (t, 2H), 3.94 (s, 3H), 3.85 (s, 3H).

Workup

  1. filtrationfiltered
  2. washwashed with H2O

Sources & evidence

ORD record
ord-f4a4998941a9452397552182412237aa
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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