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

HRID 2217053Notes

Reaction equation

HRID 2217053 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-40b346df091846579045dc676e743f09
Source dataset
uspto-grants-2006_09
Patent number
US07112701B2

Reaction notes

Loading…