Ethanol → 5,8-dimethoxy-1,4-dihydronaphthalene

HRID 1494389Notes

Reaction equation

HRID 1494389 reaction equation
CO[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:13][CH3:14].[Na].[CH2:16]([OH:18])C>O>[CH3:14][O:13][C:4]1[CH:3]=[CH:12][C:11]([O:18][CH3:16])=[C:10]2[C:5]=1[CH2:6][CH:7]=[CH:8][CH2:9]2

Participants

5

Reactant 3

HCID 702EthanolHCID 2992571,2-dimethoxynaphthaleneHCID 5360545Sodium

Product 1

HCID 117887505,8-dimethoxy-1,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethoxynaphthalene compound (66.5 mmol) was dissolved in 120 ml of ethanol. The resulting mixture was heated to reflux under nitrogen, and 11.7 g (0.51 mol) of sodium were added in portions. Stirring at reflux under nitrogen was continued until all of the solid had dissolved. The mixture then was stirred for 15 minutes at room temperature then cautiously diluted with 50 ml of water. The mixture was evaporated in vacuo to remove ethanol, and the remainder was diluted with water and extracted with ether. The organic extracts were combined, dried over sodium sulfate, and evaporated in vacuo to give 11.1 g of 5,8-dimethoxy-1,4-dihydronaphthalene as a yellow oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux under nitrogen
  3. temperatureat reflux under nitrogen
  4. dissolutionhad dissolved
  5. stirringThe mixture then was stirred for 15 minutes at room temperature
  6. customThe mixture was evaporated in vacuo
  7. customto remove ethanol
  8. additionthe remainder was diluted with water
  9. extractionextracted with ether
  10. dry with materialdried over sodium sulfate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-dba676358177465f950e40e7b73bc917
Source dataset
uspto-grants-1991_06
Patent number
US05026707

Reaction notes

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