Tributylamine → Ethyl 3-(4-methylphenyl)-2-propenoate

HRID 1156460Notes

Reaction equation

HRID 1156460 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4](Cl)=[CH:3][CH:2]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11].C(N(CCCC)CCCC)CCC>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:1]1[CH:6]=[CH:5][C:4]([CH:11]=[CH:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 78104-ChlorotolueneHCID 8821Ethyl Acrylate

Product 1

HCID 334099Ethyl 3-(4-methylphenyl)-2-propenoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.1122 g (5×10-4 mols) of palladium acetate, 6.61 ml (50 millimols) of p-tolyl chloride, 6.78 ml (62.5 millimols) of ethyl acrylate and 11.91 ml (50 millimols) of tri-n-butylamine in 100 ml of p-xylene are stirred for 3 hours at 120° C. The mixture is extracted by shaking with 50 ml of 2 N HCl, 25 ml of 2 N NaOH and 25 ml of water, and is then dried for 15 minutes with 5 g of magnesium sulphate. The crude product is distilled in vacuo. 6.08 g (64% of theory) are obtained as a colourless liquid. Analysis for C12H14O2 : calculated C 75.77%, H 7.52%; found C 75.73%, H 7.54%.

Workup

  1. extractionThe mixture is extracted
  2. dry with materialis then dried for 15 minutes with 5 g of magnesium sulphate
  3. distillationThe crude product is distilled in vacuo
  4. custom6.08 g (64% of theory) are obtained as a colourless liquid

Sources & evidence

ORD record
ord-255ff40c4f4447d18a2ce44e1c1818ba
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

Loading…