Methyl Acrylate → 3-[2,4,6-Tris(1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester

HRID 2396289Notes

Reaction equation

HRID 2396289 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH:7]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=1Br)([CH3:9])[CH3:8].[C:23](OCC)(=O)C>CN(C)C=O.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:8][CH:7]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=1[CH:23]=[CH:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH3:9]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8857Ethyl AcetateHCID 1408461-Bromo-2,4,6-triisopropylbenzene

Product 1

HCID 867492493-[2,4,6-Tris(1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of methyl acrylate (15.9 mL, 176 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.99 g, 1.4 mmol) in 125 mL dimethylformamide and 125 mL triethylamine was heated to reflux for 1 hour and then 2,4,6-triisopropylbromobenzene (10.0 g, 35 mmol) was added. Reflux was continued for 6 hours and then stirred at room temperature for 16 hours. Partitioned the reaction between water and diethyl ether. The ether layer was dried with MgSO4, filtered, and concentrated to give a brown oil. Chromatography (SiO2, eluant=5% ethyl acetate in hexanes) gave 3.80 g of 3-[2,4,6-tris(1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester as an off-white solid, mp 61°-63° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureReflux
  4. customPartitioned
  5. customthe reaction between water and diethyl ether
  6. dry with materialThe ether layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil

Sources & evidence

ORD record
ord-c18d8850ce254e7db9a122d386028f1f
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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