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

HRID 2308416Notes

Reaction equation

HRID 2308416 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[OH-].[K+].[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:21][CH2:20][CH2:19][CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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 20.2 ml (0.131 mol) of 1,6-dibromohexane, 16 g of powdered (0.242 mol KOH) caustic pot acid and 2.2 g (0.0066 mol) of tetra-n-butylammonium hydrogen sulphate are added 10 ml (0.0655 mol) of 4-phenylbutanol within 15 minutes, with stirring, at a temperature between 20 and 30° C. The reaction was spontaneously exothermic and the temperature could hardly be controlled. Towards the end of the addition, hard lumps were formed and the reaction mixture was impossible to stir.

Workup

  1. additionTowards the end of the addition
  2. customhard lumps were formed
  3. stirringto stir

Sources & evidence

ORD record
ord-4305499b7b12422ab9b847d52e5df7ee
Source dataset
uspto-grants-2004_12
Patent number
US06835857B2

Reaction notes

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