Methyl Acrylate → 2-Propenoic acid, 3-phenyl-, methyl ester

HRID 1629577Notes

Reaction equation

HRID 1629577 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10].C(N(CC)CC)C.CCCCCCCCCCCC>[Pd]>[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH:10][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7294Methyl Acrylate2×HCID 8182DodecaneHCID 8471TriethylamineHCID 11575Iodobenzene2×

Product 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
70 °C

Procedure

Starbon®-Pd(10% wt) was prepared according to example 39 and was tested in the Heck reaction of iodobenzene and methyl acrylate (see Reaction Scheme 7). Iodobenzene (8 mmol, 0.85 mL), methyl acrylate (8 mmol, 0.70 mL), triethylamine (5 mmol) and the Starbon-Pd catalyst (0.050 g) were mixed together in a microwave tube and placed in a Microwave reactor under stirring at 70° C. for 5 min. The microwave power employed in the reaction was 300 W. Dodecane (1 mmol) was employed as internal standard and results were analysed by GC. The Starbon-Pd material afforded complete (>99 mol %) conversion of the starting material with a selectivity higher than 80 mol % to the cross-coupled product, methyl cinnamate in 5 min.

Workup

  1. customwas prepared
  2. customresults

Sources & evidence

ORD record
ord-e7a9ebe2cd944e64baf1b3c096f06588
Source dataset
uspto-grants-2014_07
Patent number
US08790548B2

Reaction notes

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