Sodium Iodide → 1-(2-Methoxyethoxy)naphthalene

HRID 41843

Reaction equation

HRID 41843 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][CH2:14][CH2:15]Cl.[OH-].[Na+].[I-].[Na+]>C(O)C.C1(C)C=CC=CC=1.O>[CH3:12][O:13][CH2:14][CH2:15][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 70051-NaphtholHCID 123162-Chloroethyl methyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 206591711-(2-Methoxyethoxy)naphthaleneYield 58%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In 100 g of ethanol were dissolved 50.0 g (0.347 mol) of 1-naphthol, 34.4 g (0.364 mol) of 2-methoxyethyl chloride, 14.6 g (0.365 mol) of sodium hydroxide, and 2.6 g (0.017 mol) of sodium iodide. The solution was heated and stirred at 80° C. for 8 hours. After cooling, the solution was combined with 100 g of water and 200 g of toluene, from which an organic layer was separated. It was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution and then 4 times with 100 g of water. The organic layer was concentrated, obtaining 45 g of oily matter. On vacuum distillation (110° C./13 Pa), 41 g of the target compound was recovered (yield 58%).

Workup

  1. temperatureThe solution was heated
  2. temperatureAfter cooling
  3. customwas separated
  4. washIt was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution
  5. concentrationThe organic layer was concentrated
  6. customobtaining 45 g of oily matter
  7. distillationOn vacuum distillation (110° C./13 Pa), 41 g of the target compound
  8. customwas recovered (yield 58%)

Sources & evidence

ORD record
ord-727afadfa9894c4e90b7e1d9297cf280
Source dataset
uspto-grants-2013_09
Patent number
US08535869B2

Linked notes

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