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Water → 1-[2-Methyl-4-[2-(2-naphthalenyloxy)ethoxy]phenyl]ethanone

HRID 2225772
Notes
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Reaction equation

HRID 2225772 reaction equation
[H-].[Na+].CS([O:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)(=O)=O.[OH2:21]>CN(C)C=O>[CH3:17][C:18]1[CH:19]=[C:20]([O:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH:11]=[CH:12][C:13]=1[C:14](=[O:21])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 190043832-(2-Naphthyloxy)ethyl methanesulfonate

Product 1

HCID 190043491-[2-Methyl-4-[2-(2-naphthalenyloxy)ethoxy]phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-2-methylacetophonone (2 g) in dimethylformamide (30 mL) under argon was treated with 55% sodium hydride (0.58 g), stirred for 30 minutes and treated with 2-(2-naphthalenyloxy)ethyl methanesulfonate (3.65 g). The mixture was heated at 60° C. for 2 hours, cooled, diluted with water and filtered. The damp solids were mixed with water and excess sodium hydroxide solution, the product was extracted twice with dichloromethane, and the organic layers were washed with water. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give crude material which was crystallized from dichloromethane-diethyl ether to provide 3.5 g of 1-[2-methyl-4-[2-(2-naphthalenyloxy)ethoxy]phenyl]ethanone as a colorless solid, mp 128°-130° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. additionThe damp solids were mixed with water and excess sodium hydroxide solution
  4. extractionthe product was extracted twice with dichloromethane
  5. washthe organic layers were washed with water
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude material which
  10. customwas crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-8f0829dbede14ceca93b3e24637ec911
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05344843

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes