Acetone → HCID 14440482, compound

HRID 2255823Notes

Reaction equation

HRID 2255823 reaction equation
[OH:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[CH2:18]([O:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 213871-Hydroxypyrene

Product 1

HCID 14440482HCID 14440482, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a RB flask equipped with overhead stirrer, condenser and N2 inlet line with bubbler was added 1-hydroxypyrene (Cambridge Chemical, Inc., 5.0 g, 23 mmol), benzyl bromide (Aldrich, 15.64 g, 92 mmol, 10.94 mL), K2CO3 (Mallinckrodt, 12.72 g, 92 mmol) and acetone (100 mL). The mixture was refluxed overnight, cooled and then poured into H2O (250 mL) and extracted with EtOAc (3×100 mL). The EtOAc layers were combined and washed successively with 1N NaOH (100 mL), H2O (100 mL) and saturated NaCl solution (2×100 mL). The solution was then dried (K2CO3) and the solvent removed by rotary evaporation to give the crude product. This material was purified by passing it through a plug of SiO2 using PhCH3 as the eluting solvent. The solvent was then removed from the appropriate fractions by rotary evaporation and the solid recrystallized from CH2Cl2 /hexane to give 1.78 g (25.9% yield) of 1-benzyloxypyrene, mp 105°-106°, (C,H).

Workup

  1. customTo a RB flask equipped with overhead stirrer, condenser and N2 inlet line with bubbler
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled
  4. extractionextracted with EtOAc (3×100 mL)
  5. washwashed successively with 1N NaOH (100 mL), H2O (100 mL) and saturated NaCl solution (2×100 mL)
  6. dry with materialThe solution was then dried (K2CO3)
  7. customthe solvent removed by rotary evaporation
  8. customto give the crude product
  9. customThis material was purified
  10. customThe solvent was then removed from the appropriate fractions by rotary evaporation
  11. customthe solid recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-8ee90a5300c0412aaea736ca82e994e8
Source dataset
uspto-grants-1993_08
Patent number
US05241107

Reaction notes

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