Dichloromethane → 2-Tert-butylpyrene

HRID 1914412Notes

Reaction equation

HRID 1914412 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 t-butylchloride and 33 ml of dichloromethane was cooled to 0° C. under a nitrogen gas stream and then 2.7 g of aluminum chloride was added. This mixed solution was stirred at room temperature for 3 hours and 30 ml of water was poured into the solution, followed by extraction with 30 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 3 g (content: 65%) of 2-t-butylpyrene.

Workup

  1. extractionfollowed by extraction with 30 ml of dichloromethane
  2. washThe organic layer was washed twice with 20 ml of water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe concentrate was purified by silica gel column chromatography
  6. customvacuum-dried

Sources & evidence

ORD record
ord-a5060f0d6a7d4aab9ea4aabb807454ec
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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