Benzoyl chloride → Stilbene

HRID 1156241Notes

Reaction equation

HRID 1156241 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC(C)=CC=1>[C:2]1([CH:1]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7501StyreneHCID 7622Tributylamine

Product 1

HCID 11502StilbeneYield 89%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

7.05 g (0.05 mol) of benzoyl chloride, 6.5 g (0.0625 mol) of styrene, 8.65 g (0.05 mol) of tri-n-butylamine, 0.1122 g (0.0005 mol) of palladium acetate and 100 ml of p-xylene are introduced into a 250 ml flask and heated to 120° C., with stirring. A slight evolution of gas is observed. After the mixture has been stirred for 2 hours at 120° C., it is cooled and extracted by shaking with 2×25 ml portions of 2 N hydrochloric acid, and the organic phase is dried with magnesium sulfate. The p-xylene is distilled off and the residue is recrystallised from ethanol. 8.0 g (0.0445 mol) of stilbene are obtained as a colourless, crystalline compound, corresponding to a yield of 89% of theory; melting point 125° C.

Workup

  1. stirringAfter the mixture has been stirred for 2 hours at 120° C.
  2. temperatureit is cooled
  3. extractionextracted
  4. stirringby shaking with 2×25 ml portions of 2 N hydrochloric acid
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. distillationThe p-xylene is distilled off
  7. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-00ff5ac603094713b5f05a0d9978015b
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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