Sulfuric Acid → HCID 22625162, compound

HRID 279437Notes

Reaction equation

HRID 279437 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[O:7]=[C:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:15]([O:17][CH3:18])=[O:16].S(=O)(=O)(O)O>>[C:1]([O:5][O:6][C:8]1([O:7][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:15]([O:17][CH3:18])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6410tert-Butyl hydroperoxideHCID 288225Methyl 2-oxocycloheptane-1-carboxylate

Product 1

HCID 22625162HCID 22625162, compound

Conditions

Temperature
-5 °C

Procedure

Methyl 2,2-di(tertiary-butylperoxy)-1-cycloheptanecarboxylate was prepared by the addition of 92.28% TBHP (tertiary butyl hydroperoxide) (12.21 g, 0.1250 mol) to 99% methyl 2-oxo-1-cycloheptanecarboxylate (8.600 g, 0.0500 mol) at room temperature in a three necked 125-mL round bottomed flask equipped with a thermometer and mechanical stirrer. The solution was then cooled via a dry ice-acetone bath to −5° C. and 78% sulfuric acid (7.540 g, 0.0600 mol) was added dropwise to the solution with temperature at −5° C. Upon completion of the addition of sulfuric acid, the solution was allowed to reach 5° C. where it was maintained by an ice-water bath for ninety minutes with mechanical stirring. The reaction was transferred to a separatory funnel and the lower acidic aqueous layer separated and discarded. The organic layer was then washed with saturated NaCl solution until the aqueous washings had a pH of 4.5 or greater. The organic layer was then dried over MgSO4, filtered through a Buchner funnel and analyzed by gas chromatography. The purity was found to be 17%. This product was not purified due to low conversion of product.

Workup

  1. customequipped with a thermometer and mechanical stirrer
  2. customto reach 5° C.
  3. temperaturewas maintained by an ice-water bath for ninety minutes with mechanical stirring
  4. customThe reaction was transferred to a separatory funnel
  5. customthe lower acidic aqueous layer separated
  6. washThe organic layer was then washed with saturated NaCl solution until the aqueous washings
  7. dry with materialThe organic layer was then dried over MgSO4
  8. filtrationfiltered through a Buchner funnel
  9. customThis product was not purified due to low conversion of product

Sources & evidence

ORD record
ord-af2a5de6b99c4a27a51c3b4aafc1f4ab
Source dataset
uspto-grants-2002_03
Patent number
US06362361B1

Reaction notes

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