Sulfuric Acid → HCID 21104365, compound

HRID 1354090Notes

Reaction equation

HRID 1354090 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[Mg]Br.C[C:12]1[CH:17]=[C:16](C)[CH:15]=[CH:14]C=1Br.[Mg].C1(=O)CCCC1.OS(O)(=O)=O>CCOCC.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:14]1[CH2:15][CH2:16][CH2:17][CH:12]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 8452CyclopentanoneHCID 68503Benzene, 1-bromo-2,4-dimethyl-HCID 5462224MagnesiumHCID 178426144HCID 178426144, compound

Product 1

HCID 21104365HCID 21104365, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a 5° C. solution of 2,4-dimethylphenylmagnesium bromide (prepared from 18.5 g (100 mmol) of 2,4-dimethylbromobenzene and 2.5 g (105 mmol) of magnesium turnings) in 100 mL of ether, was added cyclopentanone (8.4 g, 100 mmol) in 25 mL of ether. The mixture was stirred at room temperature for 1 hour and was then heated under reflux for 0.5 hours. The solution was cooled in an ice bath, 60 mL of 30% aqueous H2SO4 was carefully added, and the resulting mixture was heated under reflux for 2 hours. Water was added and the mixture was extracted with ether. The ether extract was washed with aqueous sodium bisulfite solution, aqueous sodium bicarbonate, and brine, dried, and evaporated. Purification of the residue by flash chromatography (hexane) afforded 6 g of 1-(2,4-dimethyl-phenyl)cyclopentene.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 0.5 hours
  3. temperatureThe solution was cooled in an ice bath
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 2 hours
  6. extractionthe mixture was extracted with ether
  7. extractionThe ether extract
  8. washwas washed with aqueous sodium bisulfite solution, aqueous sodium bicarbonate, and brine
  9. customdried
  10. customevaporated
  11. customPurification of the residue by flash chromatography (hexane)

Sources & evidence

ORD record
ord-eb319bd8283b4aff9d05ff92d46613ef
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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