Sodium Iodide → HCID 14856822, compound

HRID 1110885Notes

Reaction equation

HRID 1110885 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].C[O-].[Na+].[I-].[Na+].Cl[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>O.CC(N(C)C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 86632-NaphtholHCID 748286-Chloro-1-hexanolHCID 10942334Sodium Methoxide

Product 1

HCID 14856822HCID 14856822, compoundYield 15.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 50.0 g (0.348 mole) of 2-naphthol, 18.8 g (0.348 mole) of sodium methoxide, 2.0 g of sodium iodide and 800 ml of dimethylacetamide was stirred at room temperature for 1 hour, 47.5 g (0.348 mole) of 6-chlorohexanol was added. The mixture was heated to reflux with stirring for two hours, allowed to cool and poured into 3 liters of water and extracted with diethylether. The ether layer was evaporated to dryness to give a solid residue which was recrystallized from methanol to give 13.3 g of 6-(2-naphthalenyloxy)hexanol, mp=64°-65° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. stirringwith stirring for two hours
  4. temperatureto cool
  5. extractionextracted with diethylether
  6. customThe ether layer was evaporated to dryness
  7. customto give a solid residue which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-ba123a42cba14f628a86c8282b522c88
Source dataset
uspto-grants-1990_12
Patent number
US04977185

Reaction notes

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