Bromocyclopentane → 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

HRID 2379576Notes

Reaction equation

HRID 2379576 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[OH:10].[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 14798Sodium HydroxideHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20 g (0.1 mol) 1-Methoxy-2-hydroxy-4-bromo-benzene (Preparation 1) was dissolved in 40 ml ethanol. Then 21 g (0.14 mol) cyclopentylbromide and a solution of 5.5 g NaOH in 6.6 ml water was added and the mixture refluxed for 13 hours. Thereafter, the solvent was removed in vacuo and the residue taken up with methylene chloride and washed (4×) with 1N NaOH. After drying over Na2SO4, the organic solvent was removed in vacuo to give the title compound as an oily product, yield: 182 g (67%).

Workup

  1. temperaturethe mixture refluxed for 13 hours
  2. customThereafter, the solvent was removed in vacuo
  3. washwashed (4×) with 1N NaOH
  4. dry with materialAfter drying over Na2SO4
  5. customthe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-e1892f8319bd4bee91aea5c469f9ab5b
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

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