Peracetic Acid → HCID 87222066, compound

HRID 1808283Notes

Reaction equation

HRID 1808283 reaction equation
[CH3:1][C:2]1[CH:3]2[CH2:9][C:6]([CH3:10])([CH2:7][CH:8]=1)[CH2:5][CH2:4]2.C(OO)(=[O:13])C.C([O-])(=O)C.[Na+]>>[CH3:1][C:2]12[O:13][CH:8]1[CH2:7][C:6]1([CH3:10])[CH2:9][CH:3]2[CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 56960321HCID 56960321, compound

Product 1

HCID 87222066HCID 87222066, compoundYield 82%

Conditions

Temperature
0 °C

Procedure

2,5-Dimethyl-bicyclo[3.2.1]oct-2-ene (800 g, 5.88 mol, obtained as above in EXAMPLE I) was fed into a solution of peracetic acid (CH3CO3H, 32%, 1.466 Kg, 6.18 mol) and sodium acetate (CH3CO2Na, 72 g, 0.882 mol), and cooled to 0° C. The reaction mixture was aged for 6 hours, and subsequently quenched with water and toluene. The reaction mixture was shaken and split. The organic layer was first washed with a solution of sodium carbonate (Na2CO3), and then with a solution of sodium sulfite (Na2SO3). Fractional distillation of the organic layer provided 2,6-dimethyl-3-oxa-tricyclo[4.2.1.0*2,4*]nonane (734 g) having a boiling point of 31° C. at a pressure of 18 mmHg

Workup

  1. customsubsequently quenched with water and toluene
  2. customsplit
  3. washThe organic layer was first washed with a solution of sodium carbonate (Na2CO3)
  4. distillationFractional distillation of the organic layer

Sources & evidence

ORD record
ord-24abc217a5a24a818a226ace148b482c
Source dataset
uspto-grants-2013_01
Patent number
US08357810B2

Reaction notes

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