Methyl iodide → 3-(4-Nitro-phenyl)-acrylic acid methyl ester

HRID 704398

Reaction equation

HRID 704398 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].CI.[C:17](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([O:12][CH3:17])=[O:11])=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-

Product 1

HCID 2196853-(4-Nitro-phenyl)-acrylic acid methyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.80 g of p-nitrocinnamic acid, 10.4 g of methyl iodide, 10.4 g of anhydrous potassium carbonate and 200 ml of acetone was stirred at room temperature for 2 days. The resultant precipitate was filtered off, the filtrate was concentrated under reduced pressure and, after addition of water, the residue was extracted with ethyl acetate. The organic layer was washed with saturated solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3.30 g of methyl 4-nitrocinnamate.

Workup

  1. filtrationThe resultant precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionafter addition of water
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bb826eff5c84b3cabe4eb8ffa8d9c7c
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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