tert-BUTYL CHLORIDE → 2-Tert-butylpyrene

HRID 1914424Notes

Reaction equation

HRID 1914424 reaction equation
[CH:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[C:17](Cl)([CH3:20])([CH3:19])[CH3:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:17]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:15]4[C:4]([CH:3]=[CH:2][CH:1]=[C:14]4[CH:13]=[CH:12]2)=[CH:5][CH:6]=[C:7]3[CH:8]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 10486tert-BUTYL CHLORIDEHCID 31423PyreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 118177682-Tert-butylpyreneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 100 g of pyrene, 55.4 g of t-butylchloride and 400 ml of dichloromethane was cooled to 0° C. under an argon gas stream and then 70.4 g of aluminum chloride was added. This mixed solution was stirred at room temperature for 5 hours and poured into 500 g of ice, followed by stirring at room temperature for 30 minutes. After the mixed solution was suction-filtered, the filtrate was extracted twice with 300 ml of dichloromethane. The organic layer was washed with 300 ml of water, dried over magnesium sulfate and then evaporated. To the concentrated residue, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. Furthermore, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. To 59.1 g of the crude product obtained by vacuum drying among 110.7 g of the crude product, 150 ml of methanol was added. The resulting solution was stirred at 85° C. for one hour, filtered and then vacuum-dried to obtain 50.3 g (content: 83%) of 2-t-butylpyrene.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. filtrationAfter the mixed solution was suction-filtered
  3. extractionthe filtrate was extracted twice with 300 ml of dichloromethane
  4. washThe organic layer was washed with 300 ml of water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. additionTo the concentrated residue, 300 ml of methanol was added
  8. stirringby stirring at 80° C.
  9. filtrationfurther filtration
  10. additionFurthermore, 300 ml of methanol was added
  11. stirringby stirring at 80° C.
  12. filtrationfurther filtration
  13. customTo 59.1 g of the crude product obtained by vacuum
  14. dry with materialdrying among 110.7 g of the crude product, 150 ml of methanol
  15. additionwas added
  16. stirringThe resulting solution was stirred at 85° C. for one hour
  17. filtrationfiltered
  18. customvacuum-dried

Sources & evidence

ORD record
ord-a221baddfb434065947810cb11dc7680
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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