Sodium Iodide → 3245-62-3

HRID 247170Notes

Reaction equation

HRID 247170 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[Br:12][CH2:13][CH2:14][CH2:15][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80011,3-DibromopropaneHCID 86632-NaphtholHCID 11430Potassium Carbonate

Product 1

HCID 41136723245-62-3

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 14.5 g (0.1 mole) of 2-naphthol, 30.3 g (0.15 mole) of 1,3-dibromopropane, 15 g of anhydrous potassium carbonate, and 1 g of sodium iodide in 125 ml of methyl ethyl ketone was stirred at reflux for one day. After cooling, the mixture was filtered to remove insolubles and the filtrate was concentrated in vacuo to dryness. The residue was dissolved in dichloromethane, washed twice with 10% aqueous sodium hydroxide, and redried thoroughly in vacuo. The residue was dissolved in hot pentane and filtered hot, and the filtrate was then concentrated under a stream of nitrogen and cooled in a refrigerator, giving the title compound, m.p. 53°-55°.

Workup

  1. temperatureat reflux for one day
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated in vacuo to dryness
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed twice with 10% aqueous sodium hydroxide
  8. customredried thoroughly in vacuo
  9. dissolutionThe residue was dissolved in hot pentane
  10. filtrationfiltered hot
  11. concentrationthe filtrate was then concentrated under a stream of nitrogen
  12. temperaturecooled in a refrigerator

Sources & evidence

ORD record
ord-7058bcf6b4854df1b84fca5dbc2c7844
Source dataset
uspto-grants-1987_11
Patent number
US04705871

Reaction notes

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