Benzene → Ethyl 3-(4-chloro-2-nitrophenyl)-2-methyl-2-propenate

HRID 1976891Notes

Reaction equation

HRID 1976891 reaction equation
[CH:1]1C=CC=CC=1.[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.CCCCCC.[C:25]([O:28][CH2:29][CH3:30])(=[O:27])[CH3:26]>>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[C:26]([CH3:1])[C:25]([O:28][CH2:29][CH3:30])=[O:27])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 796744-Chloro-2-nitrobenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 70214465Ethyl 3-(4-chloro-2-nitrophenyl)-2-methyl-2-propenate

Procedure

Into 200 ml of benzene, 10.0 g (53.8 mmol) of 4-chloro-2-nitrobenzaldehyde (manufactured by Aldrich Chemical Co., Inc.) and 18.1 g (50.0 mmol) of Wittig reagent (carbethoxyethylidene triphenylphosphorane, manufactured by Aldrich Chemical Co., Inc.) were dissolved; and the mixture was stirred at ordinary temperature for one night. After the completion of the reaction was verified by TLC, 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 13.1 g of the aimed compound were obtained as a crystal (yield: 97%).

Workup

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

Sources & evidence

ORD record
ord-db699a6678f14001ae6990c9d9748df8
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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