4-Nitrobenzaldehyde → Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate

HRID 2265101Notes

Reaction equation

HRID 2265101 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]([CH2:17][CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13].CCCCC>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[C:17](\[CH3:18])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 8003PentaneHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 11241815Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Nitrobenzaldehyde (4.20 g) and (carbetoxyethylidene)triphenylphosphorane (10 g) were dissolved in toluene (36 ml), and the obtained mixture was stirred overnight under reflux conditions. After the obtained reaction mixture was allowed to cool, N-pentane (50 ml) was added thereto, and the produced white precipitate was filtered off. The filtrate was concentrated, and N-pentane (70 ml) was added to the residue. Then, ultrasonic waves were applied to the mixture. The produced precipitate was filtered off and dried under reduced pressure to obtain crude (E)-ethyl 3-(4-nitrophenyl)-2-methylacrylate as a yellow powder.

Workup

  1. customAfter the obtained reaction mixture
  2. temperatureto cool
  3. filtrationthe produced white precipitate was filtered off
  4. concentrationThe filtrate was concentrated
  5. additionN-pentane (70 ml) was added to the residue
  6. filtrationThe produced precipitate was filtered off
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-529d30a5d75d46e7b067eccc9662a709
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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