2-(2-Naphthoxy)ethanol → 1-[4-[[2-(2Naphthalenyloxy)ethyl]thio]phenyl]ethanone

HRID 2225742Notes

Reaction equation

HRID 2225742 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].S([O-])(=O)(=O)C.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[O:28][CH2:29][CH2:30]O>CN(C)C=O.O>[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[O:28][CH2:29][CH2:30][S:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 71312-(2-Naphthoxy)ethanolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 47131801-(4-Sulfanylphenyl)ethan-1-one

Product 1

HCID 190043271-[4-[[2-(2Naphthalenyloxy)ethyl]thio]phenyl]ethanoneYield 78.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 1-(4-mercaptophenyl)ethanone (1.2 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.350 g), stirred for 15 minutes and treated with the mesylate of 2-(2-naphthyloxy)ethanol (2.2 g). The mixture was heated at 60° C. for 2 hours and diluted with water and filtered. The solids were dissolve in dichloromethane, washed once with water, dried (Na2SO4), filtered and evaporated. Crystallization from dichloromethane-hexane provided 2.0 g of 1-[4-[[2-(2naphthalenyloxy)ethyl]thio]phenyl]ethanone, mp 151°-152° C.

Workup

  1. filtrationfiltered
  2. dissolutionThe solids were dissolve in dichloromethane
  3. washwashed once with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customCrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-a7d397d79cf14a06ab5ff04a8a3154ec
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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