m-Chloroperbenzoic acid → HCID 12817969, compound

HRID 903489Notes

Reaction equation

HRID 903489 reaction equation
[CH3:1][C@@H:2]1[C:7](=[O:8])[CH2:6][C@@H:5]2[C@H:3]1[O:4]2.C(=O)(O)[O-:10].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][C@@H:2]1[O:10][C:7](=[O:8])[CH2:6][C@@H:5]2[C@H:3]1[O:4]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 56614180HCID 56614180, compound

Product 1

HCID 12817969HCID 12817969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.6 g (50 mmol) of (1S, 2S, 5R)-2-methyl-6-oxabicyclo[3.1.0]hexan-3-one (4) in 400 ml of anhydrous methylene chloride was added 15 g of sodium bicarbonate and 12.9 g (64 mmol) of 85% m-chloroperbenzoic acid. The suspension was stirred at room temperature for 72 hr and filtered through Celite Filter-Aid. The filtrate was evaporated to dryness under reduced pressure, the residue was triturated with 40 ml of methylene chloride and insolubles were removed by filtration. The filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under educed pressure. Heating at 70° (0.1 mm) removed 0.95 g of volatile material. The oily residue slowly crystallized on standing to give (1S, 2S, 6R)-2-methyl-3,7-dioxabicyclo[4.1.0]heptan-4-one: mp 51°-52°. Recrystallization from 12 ml of ether yielded end product: mp 51°-52°. Several recrystallizations from ether gave analytically pure (1S, 2S, 6R)-2-methyl-3,7-dioxabicyclo-[4.1.0]-heptan-4-one: mp 52.5°-53.5°; [α]25D +147.26 (c 0.995, MeOH).

Workup

  1. filtrationfiltered through Celite Filter-Aid
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was triturated with 40 ml of methylene chloride and insolubles
  4. customwere removed by filtration
  5. washThe filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under educed pressure
  8. temperatureHeating at 70° (0.1 mm)
  9. customremoved 0.95 g of volatile material
  10. customThe oily residue slowly crystallized

Sources & evidence

ORD record
ord-11794cbd2f29421192b722bc26e3bf23
Source dataset
uspto-grants-1980_10
Patent number
US04228080

Reaction notes

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