2-(2-Naphthoxy)ethanol → 2-[[2-(2-Naphthalenyloxy)ethyl]oxy]thiophene

HRID 2225622Notes

Reaction equation

HRID 2225622 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[O:18][CH2:19]CO>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[O:18][CH2:19][CH2:1][O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 71312-(2-Naphthoxy)ethanolHCID 856102-Methoxythiophene

Product 1

HCID 190044702-[[2-(2-Naphthalenyloxy)ethyl]oxy]thiopheneYield 49.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2-methoxythiophene (2.28 g) and 2-(2-naphthalenyloxy)ethanol (4.0 g) in benzene (35 mL) containing para-toluenesulfonic acid (0.02 g) was stirred at reflux for 3 days in a flask equipped with a Soxhlet extractor charged with 4 Å molecular sieves. The mixture was cooled, washed with 0.5N sodium hydroxide solution, dried over anhydrous magnesium sulfate (MgSO4) and evaporated. Crystallization of the residual material from ethanol (30 mL) provided 2.68 g of 2-[[2-(2-naphthalenyloxy)ethyl]oxy]thiophene as colorless flakes, mp 129°-130 ° C.

Workup

  1. temperatureat reflux for 3 days in a flask
  2. customequipped with a Soxhlet extractor
  3. additioncharged with 4 Å molecular sieves
  4. temperatureThe mixture was cooled
  5. washwashed with 0.5N sodium hydroxide solution
  6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  7. customevaporated
  8. customCrystallization of the residual material from ethanol (30 mL)

Sources & evidence

ORD record
ord-77634a073577487782f20506c3ab9fb5
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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