Dichloromethane → 2-Tert-butylpyrene

HRID 1670055Notes

Reaction equation

HRID 1670055 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 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 4.1 g of pyrene, 2 g of tert-butyl chloride and 33 ml of dichloromethane was cooled to 0° C. under a nitrogen stream, and 2.7 g of aluminum chloride was added thereto. After the mixed solution was stirred at room temperature for 3 hours, 30 ml of water was added thereto, and the mixture was extracted with 30 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography and dried under vacuum to give 3 g of 2-tert-butylpyrene (65% content).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with 30 ml of dichloromethane
  3. washThe organic layer was washed twice with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9eeb5a143fd04786a97df6559a099b2d
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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