Benzoyl chloride → Ethyl 3-phenylprop-2-enoate

HRID 1156447Notes

Reaction equation

HRID 1156447 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=C.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7622TributylamineHCID 8821Ethyl Acrylate

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoateYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3.51 g (0.025 mol) of benzoyl chloride, 3.125 g (0.03125 mol) of ethyl acrylate, 5.79 g (0.03125 mol) of tri-n-butylamine, 50 ml of toluene and 0.0561 g (0.00025 mol) of palladium acetate are introduced into a 100 ml glass flask and heated to 100° C., with stirring. A slight evolution of gas is observed. After the mixture has been stirred for 4 hours, it is cooled and the contents of the flask are extracted by shaking twice with 25 ml of 2 N hydrochloric acid at a time. The toluene phase is dried with magnesium sulfate and distilled. After the toluene has been distilled off, 2.9 g (0.0165 mol) of ethyl cinnamate are obtained, corresponding to a yield of 66% of theory; boiling point=135°-138° C./17×102Pa; nD20 =1.5592.

Workup

  1. stirringAfter the mixture has been stirred for 4 hours
  2. temperatureit is cooled
  3. extractionthe contents of the flask are extracted
  4. stirringby shaking twice with 25 ml of 2 N hydrochloric acid at a time
  5. dry with materialThe toluene phase is dried with magnesium sulfate
  6. distillationdistilled
  7. distillationAfter the toluene has been distilled off

Sources & evidence

ORD record
ord-5c1bd9e4464d40acb296569fbaeab66c
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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