Methyl Acrylate → HCID 59438476, compound

HRID 2177477Notes

Reaction equation

HRID 2177477 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]>O1CCOCC1>[CH3:17][O:16][C:12](=[O:15])[CH2:13][CH2:14][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 23423885HCID 23423885, compound

Product 1

HCID 59438476HCID 59438476, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1 g (5.828 mmol) 1-chloro-3-nitromethyl-benzene (CAS: 38362-91-3) at 0° C. in 2 ml dioxane was added 0.512 g (5.828 mmol) methyl acrylate followed by 3.3 g Amberlyst A-21. The reaction mixture was stirred overnight at room temperature, filtered and the filtrate was dried over sodium sulfate and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%) to provide 980 mg (65%) of the title compound as a colorless oil.

Workup

  1. filtrationfiltered
  2. dry with materialthe filtrate was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%)

Sources & evidence

ORD record
ord-c50d235d094b4211976ad7cdf46cde79
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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