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

HRID 236411

Reaction equation

HRID 236411 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-c6a8e0a934014b539f56ea702e6d895d
Source dataset
uspto-grants-1987_02
Patent number
US04644071

Linked notes

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