Methanol → methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate

HRID 1914695Notes

Reaction equation

HRID 1914695 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.S(Cl)(Cl)=O.[CH3:21]O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:21])=[O:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 241789753-(4-Methoxy-2-nitrophenyl)prop-2-enoic acid

Product 1

HCID 11791213methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylateYield 88%

Procedure

To a mixture of (2E)-3-(4-methoxy-2-nitrophenyl)acrylic acid (16 g, 0.067 mol) in dry MeOH (150 mL) under nitrogen is added dropwise thionyl chloride (12.3 mL, 0.169 mol) at 0° C. The reaction mixture is refluxed for 3 h then cooled to room temperature. The solvent is removed under reduced pressure and the residue is taken up in EtOAc. The organic layer is washed with 10% aqueous NaHCO3, water and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 14 g (88%) of the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.03-8.07 (m, 1H), 7.58-7.60 (m, 1H) 7.51 (s, 1H), 7.16-7.18 (m, 1H), 6.29-6.33 (m, 1H), 3.91 (s, 3H), 3.82 (s, 3H).

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. customThe solvent is removed under reduced pressure
  3. washThe organic layer is washed with 10% aqueous NaHCO3, water and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-172ddac21676421bbb8356e665a1dd0b
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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