Sodium Iodide → 1-(5-Bromopentoxy)-2-propylbenzene

HRID 247169Notes

Reaction equation

HRID 247169 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH2:2][CH3:3].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 125702-Propylphenol

Product 1

HCID 137732081-(5-Bromopentoxy)-2-propylbenzeneYield 63.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 90 g (0.66 mole) of 2-propylphenol, 300 g (1.30 mole) of 1,5-dibromopentane, 120 g of anhydrous potassium carbonate, and 9 g of sodium iodide in 1.2 l of methyl ethyl ketone was stirred at reflux for two days. After cooling, the mixture was filtered to remove insolubles and the filtrate was concentrated in vacuo. The residue was distilled under vacuum to give 120 g of the title compound as an analytically pure oil, b.p. 123°-125° at 0.1 mm Hg.

Workup

  1. temperatureat reflux for two days
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated in vacuo
  6. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-04a6579e3fa74a67af9158d7428ad544
Source dataset
uspto-grants-1987_11
Patent number
US04705871

Reaction notes

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