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

HRID 2249101Notes

Reaction equation

HRID 2249101 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-e4204399826648cbb65625575634ac01
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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