1,6-Dibromohexane → 1-[2-[(6-Bromohexyl)oxy]ethyl]-4-methoxybenzene

HRID 5217

Reaction equation

HRID 5217 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 697054-Methoxyphenethyl alcohol

Product 1

HCID 197980401-[2-[(6-Bromohexyl)oxy]ethyl]-4-methoxybenzeneYield 237.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

4-Methoxybenzeneethanol (5.0 g) and 1,6-dibromohexane (23.7 g) were stirred rapidly at RT with tetra-n-butyl ammonium bisulphate (0.94 g) and 12.5 M aqueous NaOH (30 ml) for 16 h. The mixture was diluted with H2O (125 ml), extracted with ER (3×150 ml) and the combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml), dried and evaporated to give an oil (24.6 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.30 g). T.l.c. (CX-ER (40:1)) Rf 0.33.

Workup

  1. extractionextracted with ER (3×150 ml)
  2. washthe combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b66b5c858c9f4603b5c7693801f728e2
Source dataset
uspto-grants-1993_09
Patent number
US05243076

Linked notes

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