Sodium Chloride → 2-((1-Naphthalenyloxy)methyl)oxirane

HRID 1904391Notes

Reaction equation

HRID 1904391 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]=1O.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.[OH-:17].[Na+].[Cl-].[Na+]>O1CCOCC1.O>[O:16]1[CH:14]([CH2:12][O:17][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH2:15]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7835EpichlorohydrinHCID 86632-NaphtholHCID 14798Sodium Hydroxide

Product 1

HCID 915212-((1-Naphthalenyloxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of β-naphthol (86.09 g. 0.5 mol) and epichlorohydrin (54.6 ml, 0.7 mol) in 200 ml dioxane was added a solution of sodium hydroxide (24.0 g, 0.6 mol) in 50 ml water. The mixture was refluxed for 3 hr during which time sodium chloride precipitated out. The dioxane was evaporated in vacuo and the remaining aqueous solution extracted twice with chloroform. The combined organic fractions were then washed twice with brine and dried over sodium sulfate. After removing the drying agent by filtration, the chloroform was evaporated under reduced pressure. The residual oil showed a major product with only two very minor impurities by thin layer chromatography (95:5:3 chloroform/methanol/acetic acid, Rf =0.78) and so was not purified further. Yield: 108 g.

Workup

  1. customprecipitated out
  2. customThe dioxane was evaporated in vacuo
  3. extractionthe remaining aqueous solution extracted twice with chloroform
  4. washThe combined organic fractions were then washed twice with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. customthe chloroform was evaporated under reduced pressure
  9. customso was not purified further

Sources & evidence

ORD record
ord-adba7b1d45734e59907643ae2f0dc021
Source dataset
uspto-grants-1989_06
Patent number
US04837305

Reaction notes

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