Peracetic Acid → HCID 117902423, compound

HRID 926681Notes

Reaction equation

HRID 926681 reaction equation
[CH2:1]1[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH:10]2[CH:6]([CH2:7][O:8][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=[O:18])C.[Na+].C(OO)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:10]12[CH2:9][O:8][CH2:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:15][CH2:14][CH2:13][CH:12]1[CH:11]2[O:18]1

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 10340Sodium CarbonateHCID 517045Sodium AcetateHCID 593711440785-62-4

Product 1

HCID 117902423HCID 117902423, compoundYield 271%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Muscogene (478 g, 2.4 mol), sodium acetate (63 g, 0.76 mol) and ethyl acetate (500 mL) were charged into a flask. The reaction was cooled to 0° C. While the temperature was maintained at 0° C., peracetic acid (32%, 500 mL, 2.38 mol) was dropped in over an hour and the reaction mixture was stirred for another 2 hours. Saturated sodium carbonate solution (100 mL) and toluene (50 mL) were added. The organic layer was separated and washed with brine (200 mL). The crude was purified to provide 3,15-dioxa-tricyclo[11.3.0.0*2,4*]hexadecane (462 g, ˜85% yield).

Workup

  1. temperatureWhile the temperature was maintained at 0° C.
  2. customThe organic layer was separated
  3. washwashed with brine (200 mL)
  4. customThe crude was purified

Sources & evidence

ORD record
ord-18276db1c7c84769818126808ac9b1d9
Source dataset
uspto-grants-2016_03
Patent number
US09289366B2

Reaction notes

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