Methyl 3-(4-methylphenyl)-2-propenoate → Methyl 3-(p-tolyl)propanoate

HRID 2240585

Reaction equation

HRID 2240585 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 589472Methyl 3-(4-methylphenyl)-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 9855632Methyl 3-(p-tolyl)propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.39 g of 3-p-tolyl-acrylic acid methyl ester (40aa) prepared by above Step 1 was dissolved in methanol solution (7.9 mM) under nitrogen atmosphere. Then Pd—C was added thereto, hydrogenated under a hydrogen balloon for 1 to 2 hrs at room temperature. The reaction mixture was filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with a solvent mixture mixed with EtOAc and hexane (1:10) as an eluant to give 1.24 g of 3-p-tolyl-propionic acid methyl ester (40ab) (yield: 95%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe resulting compound was purified with Silica gel column chromatography with a solvent mixture
  4. additionmixed with EtOAc and hexane (1:10) as an eluant

Sources & evidence

ORD record
ord-adf8e6ea0aee4d1181361d50396d103f
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Linked notes

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