Epichlorohydrin → 1-(2,3-Epoxypropoxy)-5,8-dihydronaphthalene

HRID 1076336Notes

Reaction equation

HRID 1076336 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.O1CCOCC1.[OH-].[Na+]>O>[O:16]1[CH2:15][CH:14]1[CH2:12][O:11][C:1]1[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 974665,8-Dihydro-1-naphthol

Product 1

HCID 110526861-(2,3-Epoxypropoxy)-5,8-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution of 15 g. (0.1 m.) of 5,8-dihydro-1-naphthol and 13.2 g. (0.14 m.) of epichlorohydrin in 38 ml. of p-dioxane, a cold solution of 4.9 g. of sodium hydroxide in 10 ml. of water is added dropwise. The mixture is refluxed three hours, cooled, and extracted with benzene. The benzene extract is washed with water, dried (MgSO4) and evaporated in vacuo to give 1-(2,3-epoxypropoxy)-5,8-dihydronaphthalene. Distillation of the crude oil at 1.2 mm., b.p. 139°-140°, gives a colorless liquid; λliq.max. film 1250, 910, 840 cm-1 (characteristic epoxy bands), CDCl3 4.13 (-C/H=C/H-), 2.5 - 3.5 (aromatic protons).

Workup

  1. temperatureThe mixture is refluxed three hours
  2. temperaturecooled
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. washis washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-16efeedb38004f988ab3ac6269071188
Source dataset
uspto-grants-1976_05
Patent number
US03956285

Reaction notes

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