Benzene → 3-(2-Nitro-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester

HRID 2269766Notes

Reaction equation

HRID 2269766 reaction equation
[CH:1]1[CH:6]=[CH:5]C=CC=1.[N+:7]([C:10]1[C:11](C=O)=[CH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:9])=[O:8].CCCCCC.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])C>>[CH2:32]([O:31][C:28](=[O:30])[C:6]([CH3:5])=[CH:1][C:15]1[CH:14]=[C:13]2[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:19][C:18]2=[CH:17][CH:16]=1)[CH3:33]

Participants

4

Reactant 3

HCID 241BenzeneHCID 120690283-Nitro-2-naphthaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 702149343-(2-Nitro-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester

Procedure

To 200 ml of benzene, 9.3 g (46 mmol) of 3-nitro-2-naphtaldehyde and 17.6 g (48.5 mmol) of Wittig reagent (carbethoxy ethylidene triphenylphosphorane) (manufactured by Aldrich Chemical Co., Inc.) were added, and the resulting mixture was stirred at room temperature for one night. The completion of the reaction was verified by TLC, and the reaction liquid was concentrated, whereby a crude product was obtained. This crude product was refined by a column chromatography (aminopropyl-modified silica gel (Fuji Silysia Chem. Co., NH-DM); developing solvent: hexane/ethyl acetate=1/1), whereby 13.0 g of the aimed compound were obtained as a crystal (yield: 96%).

Workup

  1. customthe reaction liquid
  2. concentrationwas concentrated
  3. customwhereby a crude product was obtained

Sources & evidence

ORD record
ord-1d913e397ccf4b999d44b84f7cb27897
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

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