Benzene → trans-Stilbene

HRID 444118Notes

Reaction equation

HRID 444118 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=C.[C]=O.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(C(CC)=O)C>[C:1]1(/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6325EthyleneHCID 7501Styrene2×HCID 178418416HCID 178418416, compound

Product 1

HCID 638088trans-Stilbene

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Conditions

Temperature
220 °C

Procedure

Charged in an autoclave having an inner capacity of 200 ml were 50 ml of benzene and 0.019 g of Rh6 (CO)16, followed by supply of ethylene under 30 kg/cm2 and carbon monoxide under 25 kg/cm2. The charge in the autoclave was heated at 220° C. under agitation for 7 hours. The reaction mixture was cooled and analyzed by GC and it was confirmed that 0.925 g of styrene was formed. The yield of styrene was 8900% based on the Rh atom. Furthermore, it was confirmed that 1.129 g of diethylketone and 40 mg of trans-stilbene were formed.

Workup

  1. additionCharged in an autoclave
  2. additionThe charge in the autoclave
  3. temperatureThe reaction mixture was cooled
  4. customwas formed

Sources & evidence

ORD record
ord-8f4212f978d24db6ba5961df2dc9c76c
Source dataset
uspto-grants-1981_04
Patent number
US04263212

Reaction notes

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