Sodium Thiosulfate → 2,3-Epoxy-1,2,3,4-tetrahydronaphthalene

HRID 1651611Notes

Reaction equation

HRID 1651611 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.C([O-])(O)=[O:12].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:12]1[CH:8]2[CH:7]1[CH2:6][C:5]1[C:10]([CH2:9]2)=[CH:1][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 691551,4-DihydronaphthaleneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-Dihydronaphthalene (5 g) was dissolved in methylene chloride (250 ml) and saturated aqueous NaHCO3 (280 ml). The mixture was stirred vigorously at room temperature while meta-chloroperbenzoic acid (70%, 10.0 g) was added in portions. After 1 hour, an aqueous solution of Na2S2O3 (1M, 100 ml) and methylene chloride were added. The methylene chloride layer was separated, washed with water and brine, dried (MgSO4) and evaporated to give a brownish crude mixture, which was chromatographed on a flash column (silica gel; ether: hexane=1:6) to give 2,3-epoxy-1,2,3,4-tetrahydronaphthalene (3.45 g).

Workup

  1. additionwas added in portions
  2. customThe methylene chloride layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a brownish crude mixture, which
  7. customwas chromatographed on a flash column (silica gel; ether: hexane=1:6)

Sources & evidence

ORD record
ord-deb4750df13e4a57845f19ffedad419a
Source dataset
uspto-grants-1990_05
Patent number
US04929627

Reaction notes

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