1,5-Dibromopentane → 1-[2-[(5-Bromopentyl)oxy]ethyl]-4-methoxybenzene

HRID 1084962

Reaction equation

HRID 1084962 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]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][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 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 697054-Methoxyphenethyl alcohol

Product 1

HCID 200628301-[2-[(5-Bromopentyl)oxy]ethyl]-4-methoxybenzene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-methoxybenzeneethanol (7.0 g), 1,5-dibromopentane (20 ml), 50% aqueous sodium hydroxide (30 ml) and tetrabutylammonium bisulphate (1 g) was stirred at room temperature overnight, water (100 ml) wa added and the mixture was extracted with ER (2×100 ml). The organic extracts were washed with water and brine, dried and concentrated in vacuo to give an oil which was purified by FCC eluting with hexane→hexane-ER (9:1) to give the title compound as a colourless liquid (10.5 g). T.l.c. hexane-ER (9:1) Rf 0.28.

Workup

  1. extractionthe mixture was extracted with ER (2×100 ml)
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customwas purified by FCC
  7. washeluting with hexane→hexane-ER (9:1)

Sources & evidence

ORD record
ord-480c9ad7458d45a7aff014d7786fa990
Source dataset
uspto-grants-1991_04
Patent number
US05006556

Linked notes

Loading…