Ethanol → 2-Ethoxynaphthalene

HRID 485297Notes

Reaction equation

HRID 485297 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 86632-Naphthol

Product 1

HCID 71292-Ethoxynaphthalene

Procedure

450 g of β-naphthol, 200 ml of ethanol and 50 ml of 98% sulfuric acid were mixed and after finishing the generation of heat the mixture was heated on a steam bath for 4 hours. After allowing to stand and cool, the lower layer was removed. Then the procedures wherein to the residue were added 40 ml of ethanol and 20 ml of 98% sulfuric acid, the mixture was heated on a steam bath for 3 hours and the lower layer was removed after allowing to stand and cool were repeated three times. The organic layer was washed with water to which was added an aqueous solution of sodium hydroxide (40 g of sodium hydroxide dissolved in 1 liter of water) and the mixture was warmed and shaked. While it was warm, the lower layer was removed, the upper layer was poured into an aqueous solution of sodium hydroxide and cooled to solidified. The solid was collected by filtration, washed with water and air-dried. Yield: 461 g.

Workup

  1. temperatureof heat the mixture
  2. temperaturewas heated on a steam bath for 4 hours
  3. temperaturecool
  4. customthe lower layer was removed
  5. additionThen the procedures wherein to the residue were added 40 ml of ethanol and 20 ml of 98% sulfuric acid
  6. temperaturethe mixture was heated on a steam bath for 3 hours
  7. customthe lower layer was removed
  8. temperaturecool
  9. washThe organic layer was washed with water to which
  10. additionwas added an aqueous solution of sodium hydroxide (40 g of sodium hydroxide dissolved in 1 liter of water)
  11. temperaturethe mixture was warmed
  12. temperatureWhile it was warm
  13. customthe lower layer was removed
  14. additionthe upper layer was poured into an aqueous solution of sodium hydroxide
  15. temperaturecooled to solidified
  16. filtrationThe solid was collected by filtration
  17. washwashed with water
  18. customair-dried

Sources & evidence

ORD record
ord-06e5c76d998a4cf5901931b64320f1cc
Source dataset
uspto-grants-1985_08
Patent number
US04536466

Reaction notes

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