4-Methylbenzaldehyde → Methyl 3-(4-methylphenyl)-2-propenoate

HRID 2261382Notes

Reaction equation

HRID 2261382 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:10][O:11][C:12](=[O:33])[CH:13]=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 589472Methyl 3-(4-methylphenyl)-2-propenoateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

1.0 g of p-tolualdehyde (8.3 mmol) and 4.16 g of triphenyl phosphanyliden-acetic acid methyl ester (12.45 mmol) were dissolved in methylene chloride, the reaction solution was stirred at 90° C. for overnight. After the resulting mixture was concentrated under reduced pressure, a solvent mixture mixed with EtOAc and hexane (1:7) was added thereto with stirring for 1 hr. And then white solid was removed on filter, the residue was filtered and concentrated in vacuo to give 1.39 g of 3-p-tolyl-acrylic acid methyl ester (40aa) (yield: 95%).

Workup

  1. concentrationAfter the resulting mixture was concentrated under reduced pressure
  2. additiona solvent mixture mixed with EtOAc and hexane (1:7)
  3. additionwas added
  4. stirringwith stirring for 1 hr
  5. customAnd then white solid was removed
  6. filtrationon filter
  7. filtrationthe residue was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7f99ea399024c21a7ab4ac3657f3d5b
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

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