Toluene → HCID 178444317, compound

HRID 2254978Notes

Reaction equation

HRID 2254978 reaction equation
C[Mg]I.[CH:4](/[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:22]=[CH:21][C:18](C#N)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[CH:5]\[CH2:6][CH2:7][CH3:8].C1(C)C=CC=CC=1.C([O:32][CH2:33][CH3:34])C>>[CH:4](/[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([C:33](=[O:32])[CH3:34])=[CH:21][CH:22]=2)[CH2:13][CH2:14]1)=[CH:5]\[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 178418373HCID 178418373, compoundHCID 178444327HCID 178444327, compound

Product 1

HCID 178444317HCID 178444317, compoundYield 132.1%

Procedure

A solution of methylmagnesium iodide in diethyl ether (prepared from 384 mg of magnesium shavings and 0.984 ml of methyl iodide in 30 ml of diethyl ether) was treated dropwise at room temperature with a solution of 2.0 g of p-[trans-4-(1E-pentenyl)cyclohexyl]benzonitrile. The mixture was heated to reflux for 15 minutes. Subsequently, 30 ml of toluene were added to the reaction mixture, the diethyl ether was distilled off and the mixture was heated to reflux for a further 1.5 hours. Thereafter, the reaction mixture was treated cautiously at 0° C. with saturated ammonium chloride solution and partitioned three times in diethyl ether/water. The organic extracts were washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic separation of the yellow crystalline residue (2.6 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 1.85 g (87%) of p-[trans-4-(1E-pentenyl)cyclohexyl]acetophenone as light yellow crystals; m.p. 51.2° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. distillationthe diethyl ether was distilled off
  4. temperaturethe mixture was heated
  5. temperatureto reflux for a further 1.5 hours
  6. additionThereafter, the reaction mixture was treated cautiously at 0° C. with saturated ammonium chloride solution
  7. custompartitioned three times in diethyl ether/water
  8. washThe organic extracts were washed twice with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customChromatographic separation of the yellow crystalline residue (2.6 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95)

Sources & evidence

ORD record
ord-dc85d6e9110647629c51950e97f36081
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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