1,5-Dibromopentane → 1-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene

HRID 483472

Reaction equation

HRID 483472 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Br: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:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:12][CH2:11][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 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 794063-(4-Methoxyphenyl)-1-propanol

Product 1

HCID 197980251-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzeneYield 244.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

4-Methoxybenzenepropanol (7.5 g) and 1,5 dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1.

Workup

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-536840a1ce624377a0b9d0f9af6d3ef0
Source dataset
uspto-grants-1993_07
Patent number
US05225445

Linked notes

Loading…