Dichloromethane → 2-Tert-butylpyrene

HRID 1404885Notes

Reaction equation

HRID 1404885 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].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[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

6

Reactant 4

HCID 6344DichloromethaneHCID 10486tert-BUTYL CHLORIDEHCID 31423PyreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 118177682-Tert-butylpyreneYield 142%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 150 g of pyrene, 75.52 g of t-butyl chloride and 742 ml of dichloromethane was cooled to 0° C. under a nitrogen stream, and 98.9 g of aluminum chloride was added. After this mixed solution was stirred at room temperature for 3 hours, 1100 ml of water was added, and this was extracted with 1100 ml of dichloromethane. The organic layer was washed with 750 ml of water three times, dried with magnesium sulfate, and evaporated, and this was purified by methanol washing, and filtered. After the resultant was vacuum dried, 272 g (content 79.2%) of 2-t-butylpyrene was obtained.

Workup

  1. additionwas added
  2. extractionthis was extracted with 1100 ml of dichloromethane
  3. washThe organic layer was washed with 750 ml of water three times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customthis was purified by methanol washing
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-75dd3e574f3f48918ace4f456fc69998
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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