m-Chloroperbenzoic acid → HCID 10035684, compound

HRID 465574Notes

Reaction equation

HRID 465574 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)Cl>[O:22]1[CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 111830362H-Pyran, 2-(5-hexenyloxy)tetrahydro-

Product 1

HCID 10035684HCID 10035684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.57 g of 6-(2-tetrahydropyranyloxy)-hex-1-ene in 200 ml of methylene chloride is added 10.8 g m-chloroperbenzoic acid and the mixture is stirred at room temperature for 18 h. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution followed by saturated sodium sulfite solution. The organic phase is dried, filtered and evaporated to give a clear oil which is purified by chromatography over silica gel using hexane/ether (4:1) as eluent to obtain 1,2-epoxy-6-(2-tetrahydropyranyloxy)-hexane; IR (CH2CH2): 1450, 1135, 1033 cm-1.

Workup

  1. customThe reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give a clear oil which
  6. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-711dedf7c98c4c1084ea8015e9c12dff
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…