Benzyl Chloride → 6-(Benzyloxy)naphthalen-2-OL

HRID 1656813Notes

Reaction equation

HRID 1656813 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:14])[CH:10]=2)[CH:5]=1.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:15]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:14])[CH:10]=2)[CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 144964736-(Benzyloxy)naphthalen-2-OL

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (12 g, 0.3 mol 60% in mineral oil) in 600 ml toluene and 400 ml dimethyl formamide was added 2,6-dihydroxynaphthalene (80 g, 0.5 mol) and the mixture was heated to reflux over a thirty minute period. Benzyl chloride (65 ml, 71.5 g, 0.56 mol) was added dropwise and the mixture was refluxed for 10 hours. After cooling to room temperature, the mixture was washed 6 times with water to remove the dimethyl formamide. The resulting toluene solution was washed twice with 150 ml 0.5N sodium hydroxide to remove unreacted starting material and then with water and dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated to 150 ml. The solid which had crystallized was collected by vacuum filtration and washed with a small amount of toluene to yield 2-benzyloxy-6-hydroxynaphthalene.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux over a thirty minute period
  3. temperaturethe mixture was refluxed for 10 hours
  4. washthe mixture was washed 6 times with water
  5. customto remove the dimethyl formamide
  6. washThe resulting toluene solution was washed twice with 150 ml 0.5N sodium hydroxide
  7. customto remove unreacted
  8. dry with materialwith water and dried over anhydrous magnesium sulfate
  9. customThe magnesium sulfate was removed by filtration
  10. concentrationthe filtrate was concentrated to 150 ml
  11. customThe solid which had crystallized
  12. filtrationwas collected by vacuum filtration
  13. washwashed with a small amount of toluene

Sources & evidence

ORD record
ord-997e34f9722b46a6b68eb62af6a39ff0
Source dataset
uspto-grants-1993_10
Patent number
US05254747

Reaction notes

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