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

HRID 2376677Notes

Reaction equation

HRID 2376677 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]1([CH3:33])[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1>ClCCl>[C:25]1([CH3:33])[CH:30]=[CH:29][C:28](/[CH:31]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:27][CH:26]=1

Participants

4

Reactant 2

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

Product 1

HCID 5314312Methyl (2E)-3-(4-methylphenyl)-2-propenoateYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of methyl (triphenylphosphoranylidene)acetate and 720 mg of p-toluenealdehyde are dissolved in 10 ml of dichloromethane and stirred at room temperature for twelve hours. Then, 4 g of kieselguhr are added, and the solvent is removed in vacuo. The resulting residue is purified on silica gel with n-heptane:ethyl acetate=4:1 as eluent. 850 mg of methyl trans-3-p-tolylacrylate are obtained as an oil.

Workup

  1. additionThen, 4 g of kieselguhr are added
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified on silica gel with n-heptane

Sources & evidence

ORD record
ord-bcbe795c035c48dda5c6d093849767df
Source dataset
uspto-grants-2008_12
Patent number
US07468369B2

Reaction notes

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