Sodium Iodide → HCID 476768, compound

HRID 1645890Notes

Reaction equation

HRID 1645890 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].Cl[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24].[I-].[Na+]>CN(C)C=O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 71034-HydroxybiphenylHCID 748286-Chloro-1-hexanolHCID 10942334Sodium Methoxide

Product 1

HCID 476768HCID 476768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 34.0 g (0.2 mole) or p-phenylphenol (Eastman) and 10.8 g (0.2 mole) of sodium methoxide (MCB) in 500 ml of dry dimethylformamide is heated and stirred on a steam bath for 0.5 hour, after which 27.3 g (0.2 mole) of 6-chlorohexan-1ol (MCB) and about 2 g of sodium iodide are added. The mixture is heated to reflux with stirring, and then allowed to cool to room temperature. The reaction mixture is partitioned between ether/acetone and water, and the organic phase is extracted with base, washed with water and brine, dried (Na2SO4), and the solvent evaporated. The resultant white solid product is recrystallized twice from methanol/acetone, to give the desired product, m.p. 103-105° C.

Workup

  1. temperatureis heated
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. stirringwith stirring
  5. customThe reaction mixture is partitioned between ether/acetone and water
  6. extractionthe organic phase is extracted with base
  7. washwashed with water and brine
  8. dry with materialdried (Na2SO4)
  9. customthe solvent evaporated
  10. customThe resultant white solid product is recrystallized twice from methanol/acetone

Sources & evidence

ORD record
ord-8ba63439baa24e06ad5105ad6ee40fb6
Source dataset
uspto-grants-1993_01
Patent number
US05177108

Reaction notes

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