4-Nitrobenzaldehyde → Ethyl 3-(4-nitrophenyl)-2-propenoate

HRID 1368885Notes

Reaction equation

HRID 1368885 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([CH:17]1CP(C2C=CC=CC=2)C(C2C=CC=CC=2)(C2C=CC=CC=2)C1=C)([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)Cl>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:17][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 66938305Carboethoxy-methylenetriphenylphospholan

Product 1

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrobenzaldehyde (1 g) was dissolved in methylene chloride (20 ml), and the reaction system was cooled to 0° C. The solution was added with carboethoxy-methylenetriphenylphospholan (2.56 g) and stirred at 0° C. for 1 hour. The reaction system was concentrated under reduced pressure without any treatment, and the residue was purified by silica gel column chromatography (50 g, hexane:ethyl acetate=4:1) to obtain ethyl 3-(4-nitrophenyl)acrylate (1.27 g, 86%).

Workup

  1. concentrationThe reaction system was concentrated under reduced pressure without any treatment
  2. customthe residue was purified by silica gel column chromatography (50 g, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7555ad533a0e44f08bf7fe3fbb6decdd
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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