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

HRID 1030633Notes

Reaction equation

HRID 1030633 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]=[CH:13]1>C(#N)C>[O:9]1[CH:19]2[CH:18]1[CH2:17][C:16]1[C:21]([CH2:20]2)=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 691551,4-DihydronaphthaleneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthaleneYield 65.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of metachloroperbenzoic acid (55%, 22.8 g) in acetonitrile (190 ml) was added dropwise over 15 min to a solution of 1,4 dihydro naphthalene (7.86 g) in acetonitrile (100 ml) at 0° C. The resulting mixture was stirred for 6 hours at room temperature. The mixture was concentrated to about 50 ml under reduced pressure, diluted with methylene chloride and filtered. The filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium hydrogenocarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The resulting solid (8.45 g) was chromatographed (silica gel, 150 g, elution with ethyl acetate:hexane, 1:9) to give the title compound as a solid (5.81 g).

Workup

  1. concentrationThe mixture was concentrated to about 50 ml under reduced pressure
  2. additiondiluted with methylene chloride
  3. filtrationfiltered
  4. washThe filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium hydrogenocarbonate, saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid (8.45 g) was chromatographed
  8. wash(silica gel, 150 g, elution with ethyl acetate:hexane, 1:9)

Sources & evidence

ORD record
ord-c5112653c9b44b219868a164619eb38a
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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