Benzene → HCID 13280229, compound

HRID 1289266Notes

Reaction equation

HRID 1289266 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:10])/[C:6](=[CH:8]/[CH3:9])/[CH3:7].[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(=S)=S.CCCCCC.O>[CH3:7][CH:6]1[CH:8]([CH3:9])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]1=[O:10]

Participants

8

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 5325503(2E)-2-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13280229HCID 13280229, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent2×HCID 8058HexaneSolvent2×

Procedure

Aluminum trichloride in an amount of 30.7 g (250 mmol) was suspended in 150 mL of dried carbon disulfide (dried and distilled on calcium hydride) and was brought to an ice-cooling temperature. Then, 25.1 g (212 mmol) of tigloyl chloride was mixed with 16.6 g (212 mmol) of benzene, and to the resultant mixture was added dropwise the above-produced carbon disulfide solution, followed by continuous stirring at room temperature. As the result, a yellow solution was gradually produced. The solution was allowed to stand overnight, with the result that the solution was separated into two phases including a brown phase and a colorless phase. The solution was allowed to react for another 5 hours under refluxing. The resultant reaction mixture was brought back to room temperature and thereafter, was poured onto the mixture of 250 g of water and 250 mL of concentrated hydrochloric acid, followed by stirring for about one hour. Then, the resultant product was subjected to extraction and separation four times repeatedly with 200 mL each of ether. The ether phases thus produced were combined together, and dried with calcium chloride anhydride as the drying agent. After filtering away the used drying agent, the ether was distilled away and the brown viscous oil was obtained. Because of its being readily soluble in hexane, the oil was again dissolved in hexane, and the resultant solution was washed twice with 150 mL each of saturated aqueous solution of sodium carbonate and twice with 150 mL each of saturated aqueous solution of sodium chloride, and dried with magnesium sulfate anhydride. By distilling away the hexane, there was obtained 19.9 g of 2,3-dimethylindane-1-one.

Workup

  1. temperaturecooling temperature
  2. customAs the result, a yellow solution was gradually produced
  3. customwith the result that the solution
  4. customwas separated into two phases
  5. customto react for another 5 hours
  6. temperatureunder refluxing
  7. customThe resultant reaction mixture
  8. customwas brought back to room temperature
  9. stirringby stirring for about one hour
  10. extractionThen, the resultant product was subjected to extraction and separation four times repeatedly with 200 mL each of ether
  11. customThe ether phases thus produced
  12. dry with materialdried with calcium chloride anhydride as the drying agent
  13. filtrationAfter filtering away the
  14. customused drying agent
  15. distillationthe ether was distilled away
  16. customthe brown viscous oil was obtained
  17. washthe resultant solution was washed twice with 150 mL each of saturated aqueous solution of sodium carbonate and twice with 150 mL each of saturated aqueous solution of sodium chloride
  18. dry with materialdried with magnesium sulfate anhydride
  19. distillationBy distilling away the hexane

Sources & evidence

ORD record
ord-d81617b54efc4949a06487e9b12433df
Source dataset
uspto-grants-1998_05
Patent number
US05747614

Reaction notes

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