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

HRID 1781484Notes

Reaction equation

HRID 1781484 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.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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-a415a2aa4c31427b970172b8ba449f65
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

Loading…