Methyl 2-nitroacetate → (E)-Methyl-2-nitro-3-(2,4,6-trimethoxyphenyl)acrylate

HRID 553269Notes

Reaction equation

HRID 553269 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:4]=1[CH:5]=O.S([O-])([O-])(=O)=O.[Mg+2].C([O-])(=O)C.[NH4+].[N+:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])([O-:28])=[O:27]>ClCCl.O>[CH3:33][O:32][C:30](=[O:31])/[C:29](/[N+:26]([O-:28])=[O:27])=[CH:5]\[C:4]1[C:3]([O:2][CH3:1])=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 17206Methyl 2-nitroacetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 700192,4,6-TrimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 86641484(E)-Methyl-2-nitro-3-(2,4,6-trimethoxyphenyl)acrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2,4,6-trimethoxybenzaldehyde (20.75 g, 0.105 mol) was dissolved in dichloromethane (300 mL) and to this solution magnesium sulphate (15 g, 0.124 mol), ammonium acetate (10 g, 0.129 mol) and methyl nitroacetate (12.60 g, 0.105 mol) were added and stirred at room temperature for 2 hours. At the end of two hours, water (300 mL) was added to the reaction mass, the organic layer was separated and the aqueous layer extracted with dichloromethane (2×100 mL). The organic layers were combined and concentrated under reduced pressure to give a solid, which was crystallized from methanol (100 mL).

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×100 mL)
  4. concentrationconcentrated under reduced pressure
  5. customto give a solid, which
  6. customwas crystallized from methanol (100 mL)

Sources & evidence

ORD record
ord-12de784fbfca4daea0727a347296f570
Source dataset
uspto-grants-2011_05
Patent number
US07951961B2

Reaction notes

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