1,4-Dibromobutane → [4-(4-Bromobutoxy)phenyl](phenyl)methanone

HRID 2295152Notes

Reaction equation

HRID 2295152 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>CCCCC>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 21469788[4-(4-Bromobutoxy)phenyl](phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Combine 4-hydroxybenzophenone (14.11 g, 71.2 mmol) and aqueous 1M sodium hydroxide solution (70 mL). Add 1,4-dibromobutane (43.4 g, 200 mmol). Heat the reaction mixture to reflux. After 20.5 hours, cool to ambient temperature. Add pentane (100 mL) and again heat to reflux. After 0.5 hours, cool to ambient temperature to give a solid. Collect the solid by filtration. recrystallize the solid from ethanol to give the title compound: mp; 42°-43° C.

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureto reflux
  3. waitAfter 0.5 hours
  4. temperaturecool to ambient temperature
  5. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. customrecrystallize the solid from ethanol

Sources & evidence

ORD record
ord-aa8bc67f58d44409a33606e32c856f62
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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