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

HRID 2308414Notes

Reaction equation

HRID 2308414 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.C1(C)C=CC=CC=1>[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

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14797Potassium HydroxideHCID 76889Benzenebutanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 10 ml (0.0655 mol) of 4-phenylbutanol and 20 ml of toluene is added within 15 minutes, with stirring, to a mixture of 20.2 ml (0.131 mol) of 1,6-dibromohexane, 16 g of powdered (0.242 mol KOH) caustic potash, 2.2 g (0.0066 mol) tetra-n-butylammonium hydrogen sulphate and 50 ml of toluene, at a temperature between 25 and 30° C. After it has all been added the mixture is rinsed with 5 ml of toluene and stirred for 2 hours at a temperature between 25 and 30° C. Then 75 ml of water are added, the organic phase is separated off and washed twice with 50 ml of water. The organic phase is concentrated under reduced pressure using the rotary evaporator and the residue is fractionally distilled under a high vacuum (p<0.1 mbar). 14.62 g (71% of theory) of the title compound are obtained as a colorless oil.

Workup

  1. additionis added within 15 minutes
  2. additionall been added the mixture
  3. washis rinsed with 5 ml of toluene
  4. additionThen 75 ml of water are added
  5. customthe organic phase is separated off
  6. washwashed twice with 50 ml of water
  7. concentrationThe organic phase is concentrated under reduced pressure
  8. customthe rotary evaporator
  9. distillationthe residue is fractionally distilled under a high vacuum (p<0.1 mbar)

Sources & evidence

ORD record
ord-2cab214b76df4fab9cc4189f68396c83
Source dataset
uspto-grants-2004_12
Patent number
US06835857B2

Reaction notes

Loading…