1,6-Dibromohexane → 1-[4-[(6-Bromohexyl)oxy]butyl]benzene

HRID 1936209Notes

Reaction equation

HRID 1936209 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14797Potassium HydroxideHCID 76889Benzenebutanol

Product 1

HCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

To a mixture of 5 ml (32.75 mmol) 4-phenylbutanol with 10.1 ml (65.66 mmol) 1,6-dibromohexane is added 8 g (121.2 mmol) powdered KOH and 1.112 g (3.28 mmol) tetrabutylammonium hydrogen sulfate. After allowing the suspension to stir for 20 hr at room temperature, it is filtered and the filtrate dissolved in 50 ml Et2O. The resulting solution is washed with water, dried on anhydrous Na2SO4, the Et2O evaporated and the residue distilled in vacuum (0.1 mmHg), a first fraction up to 100° C. of a mixture of starting products and a second fraction at 150° C. of 4-(6-bromohexyloxy)butylbenzene weighing 7.60 g (74.4 %) being collected.

Workup

  1. additionis added 8 g (121.2 mmol)
  2. filtrationit is filtered
  3. dissolutionthe filtrate dissolved in 50 ml Et2O
  4. washThe resulting solution is washed with water
  5. dry with materialdried on anhydrous Na2SO4
  6. customthe Et2O evaporated
  7. distillationthe residue distilled in vacuum (0.1 mmHg)
  8. additiona first fraction up to 100° C. of a mixture of starting products
  9. customa second fraction at 150° C. of 4-(6-bromohexyloxy)butylbenzene weighing 7.60 g (74.4 %) being collected

Sources & evidence

ORD record
ord-4b68e9280b4b424aad87f3e13547ea85
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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