1,4-Dihydronaphthalene → 2,3-Epoxy-1,2,3,4-tetrahydronaphthalene

HRID 46498Notes

Reaction equation

HRID 46498 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[O:19]1[CH:7]2[CH2:6][C:5]3[C:10]([CH2:9][CH:8]12)=[CH:1][CH:2]=[CH:3][CH:4]=3

Participants

4

Reactant 2

HCID 691551,4-DihydronaphthaleneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1,4-dihydronaphthalene (32.5 g, 0.25 M) in 300 ml chloroform is cooled in an ice bath and, while stirring, is treated portionwise with 61 g (~20% excess) of 85% m-chloroperbenzoic acid. The mixture is stirred overnight at room temperature. After cooling in an ice bath, the solids are removed by filtration. The filtrate is washed twice with 5% K2CO3 solution, dried over MgSO4, filtered and the solvent is removed in vacuo leaving 37.7 g of yellow partially crystalline material. This is distilled from a small amount of solid K2CO3. After removal of some low boiling material, 16.0 g (44%) of the desired epoxide is collected, boiling point 95°-110° at 0.1 mm.

Workup

  1. stirringThe mixture is stirred overnight at room temperature
  2. temperatureAfter cooling in an ice bath
  3. customthe solids are removed by filtration
  4. washThe filtrate is washed twice with 5% K2CO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. customleaving 37.7 g of yellow partially crystalline material
  9. distillationThis is distilled from a small amount of solid K2CO3
  10. customAfter removal of some low boiling material, 16.0 g (44%) of the desired epoxide
  11. customis collected

Sources & evidence

ORD record
ord-7e95e19e1a454d74825019b67d675de9
Source dataset
uspto-grants-1979_11
Patent number
US04173640

Reaction notes

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