Methanol → Methyl 2-ethoxy-4,5-dinitrobenzoate

HRID 1012125Notes

Reaction equation

HRID 1012125 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([O:20][CH2:21][CH3:22])[CH:9]=1)([O-:7])=[O:6].[CH3:23]O>>[CH3:23][O:13][C:12](=[O:14])[C:11]1[CH:15]=[C:16]([N+:17]([O-:19])=[O:18])[C:8]([N+:5]([O-:7])=[O:6])=[CH:9][C:10]=1[O:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 858173894,5-dinitro-2-ethoxy-benzoic Acid

Product 1

HCID 71418202Methyl 2-ethoxy-4,5-dinitrobenzoate

Procedure

Thionyl chloride (315 μl, 4.30 mmol) was slowly added to a mixture of 4,5-dinitro-2-ethoxy-benzoic acid (1.00 g, 3.91 mmol) in methanol (10 mL) at r.t. The mixture was stirred for 16 h, then reduced in vacuo azeotroping with toluene. The residue was then purified by column chromatography using P.E.-EtOAc (1:0-1:1) to give the title compound (606 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.00 (s, 1H), 4.35 (q, 2H), 3.85 (s, 3H), 1.35 (t, 3H).

Workup

  1. customazeotroping with toluene
  2. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-ce0fe3637ff34fada82e46e16fba09fb
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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