Dichloromethane → 2-Tert-butylpyrene

HRID 1404881Notes

Reaction equation

HRID 1404881 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-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. After this mixed solution was stirred at room temperature for 3 hours, 30 ml of water was added, and this was extracted with 30 ml of dichloromethane. The organic layer was washed with 20 ml of water two times, dried with magnesium sulfate, and evaporated. This was purified by silica gel column chromatography, and vacuum-dried to obtain 3 g (content 65%) of 2-t-butylpyrene.

Workup

  1. additionwas added
  2. extractionthis was extracted with 30 ml of dichloromethane
  3. washThe organic layer was washed with 20 ml of water two times
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customThis was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-043b412e1d53458ab1b8af1b2301f845
Source dataset
uspto-grants-2014_12
Patent number
US08916275B2

Reaction notes

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