Water → 1-(2-Methoxyethoxy)naphthalene

HRID 2367904Notes

Reaction equation

HRID 2367904 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+].O>C(O)C.[I-].[Na+].C1(C)C=CC=CC=1>[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 962WaterHCID 70051-NaphtholHCID 123162-Chloroethyl methyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 206591711-(2-Methoxyethoxy)naphthaleneYield 584.2%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In 100 g of ethanol were dissolved 50.0 g (0.0347 mol) of 1-naphthol, 34.4 g (0.0364 mol) of 2-methoxyethyl chloride, 14.6 g (0.0364 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 at 110° C. and 13 Pa, 41 g of 1-(2-methoxyethoxy)naphthalene was obtained (yield 58%). Next 5.0 g (0.024 mol) of 1-(2-methoxyethoxy)naphthalene was dispersed in 10 g of Eaton's Reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution), to which 5.1 g (0.049 mol) of tetramethylene sulfoxide was added dropwise and mixed. The solution was matured overnight at room temperature and combined with 30 g of water and 30 g of diisopropyl ether, from which a water layer was separated. The water layer was again washed with 30 g of diisopropyl ether. This aqueous solution was combined with an aqueous solution (corresponding to 0.007 mol) of sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate which was synthesized according to the formulation described in JP-A 2007-145797, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water, and the solvent was distilled off in vacuum. The residue was poured into isopropyl ether for crystallization. Subsequent filtration and drying gave the target compound. White crystal, 7.9 g, yield 94%.

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 at 110° C.

Sources & evidence

ORD record
ord-cccccc6e85af4a119bce72a29d086994
Source dataset
uspto-grants-2014_04
Patent number
US08703384B2

Reaction notes

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