Sulfuric Acid → HCID 22625165, compound

HRID 279436Notes

Reaction equation

HRID 279436 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH3:16])=[O:14].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])[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH3:16])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6410tert-Butyl hydroperoxideHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 22625165HCID 22625165, compound

Conditions

Temperature
-5 °C

Procedure

Methyl 2,2-di(tertiary-butylperoxy)-1-cyclopentanecarboxylate was prepared by the addition of 92.28% TBHP (tertiary butyl hydroperoxide) (36.62 g, 0.3750 mol) to 97% methyl 2-oxo-1-cyclopentanecarboxylate (14.65 g, 0.1000 mol) at room temperature in a three necked 250-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 (15.09 g, 0.1200 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 three hours 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 4.0 to 4.5. The organic layer was then dried over MgSO4, filtered through a Buchner funnel and analyzed for purity by gas chromatography (88% by area): 1H NMR (300 MHz, CDCl3) δ 3.7 (s, 3H, CH3), 3.3-3.4 (m, 1H, cyclic H), 1.9-2.2 (m, 6H, cyclic H), 1.3 (s, 9H, CH3), 1.2 (s, 9H, CH3); 13C NMR (75 MHz, CDCl3) δ 172.4 (C═O). 116.9 (O—C—O, cyclic), 79.7 (CCH3)3), 79.4 (C(CH3)3), 51.1 (CH, cyclic), 49.1 (CH3—O), 32.9 (CH2, cyclic), 27.7 (CH2, cyclic), 26.2 (C(CH3)3, (2x)), 22.1 (CH2, cyclic); IR (neat) 1740, 1364, 1198, 878 cm−1.

Workup

  1. customequipped with a thermometer and mechanical stirrer
  2. customto reach 5° C.
  3. temperaturewas maintained by an ice-water bath for three hours 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

Sources & evidence

ORD record
ord-1a9384c789254b9582324845f17f8fc8
Source dataset
uspto-grants-2002_03
Patent number
US06362361B1

Reaction notes

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