Methyl Acrylate → Methyl sorbate

HRID 1658903Notes

Reaction equation

HRID 1658903 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([O:24][CH3:25])(=[O:23])/[CH:21]=[CH:22]/[CH:2]=[CH:1]/[CH3:6]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 7622TributylamineHCID 11776Triphenylphosphine

Product 1

HCID 5323650Methyl sorbateYield 4%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

Quantities of 1.1 grams palladium acetate, 5.25 grams triphenyl phosphine, 42 cc alkyl bromide, 45 cc methyl acrylate and 119 cc tributyl amine are introduced into a reactor chamber and heated to 120°C for 27 hours. The resulting reaction mass is extracted with ether followed by distillation yielding 2.9 grams (4% yield) of methyl sorbate and alkyl-tributyl ammonium bromide as the major product.

Workup

  1. customThe resulting reaction mass
  2. extractionis extracted with ether
  3. distillationfollowed by distillation

Sources & evidence

ORD record
ord-779a5bf066354e3b84e1232dd2e251c3
Source dataset
uspto-grants-1976_06
Patent number
US03966798

Reaction notes

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