m-Chloroperbenzoic acid → HCID 13882254, compound

HRID 979535Notes

Reaction equation

HRID 979535 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.C([O-])(O)=[O:15].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[O:15][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13882253HCID 13882253, compound

Product 1

HCID 13882254HCID 13882254, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Fluorophenyl)cyclohexene of Example 1(a) [6.76 g; 0.038 mole] was dissolved in a two-phase system consisting of 350 ml of CH2Cl2 and 110 ml of 0.5M NaHCO3. m-Chloroperbenzoic acid (7.80 g of 85%; 0.38 mole) was then added portionwise with vigorous mechanical stirring. After 2 hours TLC indicated that the reaction was complete. The organic layer was separated and washed with 100 ml of N NaOH and 100 ml of water. Drying and concentration under reduced pressure gave an oil which amounted to 6.34 g (86%) after distillation, b.p. 113°/0.075 mm (Kugelrohr). A small portion was chromatographed over silica gel (CHCl3) to remove traces of polar impurities and distilled again to provide the sample of 1-(2-fluorophenyl)cyclohexene oxide.

Workup

  1. customThe organic layer was separated
  2. washwashed with 100 ml of N NaOH and 100 ml of water
  3. customDrying
  4. concentrationconcentration under reduced pressure
  5. customgave an oil which
  6. distillationafter distillation, b.p. 113°/0.075 mm (Kugelrohr)
  7. customA small portion was chromatographed over silica gel (CHCl3)
  8. customto remove traces of polar impurities
  9. distillationdistilled again

Sources & evidence

ORD record
ord-1f43356a605244f6aa1ff9837558fd9d
Source dataset
uspto-grants-1987_05
Patent number
US04668690

Reaction notes

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