Ethanol → 1-(2-Methoxyethoxy)naphthalene

HRID 1849955Notes

Reaction equation

HRID 1849955 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+].C(O)C>[I-].[Na+].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 702EthanolHCID 70051-NaphtholHCID 123162-Chloroethyl methyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 206591711-(2-Methoxyethoxy)naphthaleneYield 77.8%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, a mixed solution of 1500 g of 1-naphthol, 1032 g of 2-methoxyethyl chloride, 460 g of sodium hydroxide, 78 g of sodium iodide, and 3000 g of ethanol was stirred for 37 hours with heating at 80° C. After cooling, 3000 g of water and 5000 g of toluene were added to the mixed solution, and then the organic layer was separated and washed by 1800 g of an aqueous sodium hydroxide (concentration of 5% by mass) for five times. Then, after washed by 1800 g of water for four times, the organic layer was concentrated to obtain 1835 g of an oily substance. This was distilled under reduced pressure (at 110° C. and 13 Pa) to obtain 1637 g of the intended product (Yield 77%).

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. washwashed by 1800 g of an aqueous sodium hydroxide (concentration of 5% by mass) for five times
  4. washThen, after washed by 1800 g of water for four times
  5. concentrationthe organic layer was concentrated
  6. customto obtain 1835 g of an oily substance
  7. distillationThis was distilled under reduced pressure (at 110° C. and 13 Pa)

Sources & evidence

ORD record
ord-32604d41b6e6484aadd5edc24e2df79e
Source dataset
uspto-grants-2015_02
Patent number
US08956803B2

Reaction notes

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