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

HRID 893771Notes

Reaction equation

HRID 893771 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-Methoxybenzenethanol (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 12.5M 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 mol), 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 colorless 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 mol)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-d3b6f8eec5934c4abf30cdfead55e14c
Source dataset
uspto-grants-1992_06
Patent number
US05126375

Reaction notes

Loading…