2-Chloroethanol → 2-(2-Naphthoxy)ethanol

HRID 846025Notes

Reaction equation

HRID 846025 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].[OH-].[Na+].Cl[CH2:15][CH2:16][OH:17].C1(C)C=CC=CC=1>CS(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][CH2:15][CH2:16][OH:17]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 1140TolueneHCID 86632-NaphtholHCID 14798Sodium Hydroxide

Product 1

HCID 71312-(2-Naphthoxy)ethanolYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The reaction set-up consisted of a three necked round bottom flask, equipped with a thermometer, condenser and a mechanical stirrer, and a dropping funnel. 2-Naphthol, 100 g (0.6936 moles), was dissolved in 60 mL of dimethyl sulfoxide. Sodium hydroxide, 27.7 g (0.6936 moles), was carefully added to the solution. Then 2-chloroethanol, 61.4 g (0.7629 moles), was slowly added, keeping the reaction temperature at 80 C. The reaction was followed by GC. After 80% conversion was achieved, the reaction was worked-up by adding toluene and extracting the unreacted naphthol with 5% aqueous NaOH. The product was then recrystallized in ethanol or distilled under vacuum (70-80% yield).

Workup

  1. customequipped with a thermometer, condenser and a mechanical stirrer, and a dropping funnel
  2. extractionextracting the unreacted naphthol with 5% aqueous NaOH
  3. customThe product was then recrystallized in ethanol
  4. distillationdistilled under vacuum (70-80% yield)

Sources & evidence

ORD record
ord-7dc93873ba874e34a7816e433c59cf73
Source dataset
uspto-grants-1992_08
Patent number
US05135774

Reaction notes

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