Hydrogen Peroxide → t-Butyl 3-(1-carboxycyclopentyl)propanoate

HRID 861692Notes

Reaction equation

HRID 861692 reaction equation
C([C:4]1([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=O)C.OO.S(=O)(=O)(O)[OH:23]>C(O)(C)(C)C>[C:16]([O:15][C:13]([CH2:12][CH2:11][C:4]1([C:5]([OH:10])=[O:23])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 109892762-Acetyl-2-[2-(tert-butoxycarbonyl)ethyl]cyclohexanone

Product 1

HCID 11010130t-Butyl 3-(1-carboxycyclopentyl)propanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of crude 2-acetyl-2-[2-(tert-butoxycarbonyl)-ethyl]cyclohexanone (see Preparations 1 and 2) (42 g, 0.15 mol) in t-butanol (84 ml) was cautiously added a 30% aqueous hydrogen peroxide solution (21 ml, 0.187 mol) and conc. sulphuric acid (0.25 ml, 98% w/w) at room temperature, maintaining the reaction temperature below 50° C. during the addition. The mixture was stirred at room temperature for 18 hours, partitioned between dichloromethane (100 ml) and water (100 ml), and the layers separated. The dichloromethane layer was washed with 5% aqueous sodium sulphite solution (50 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a pale yellow solid, (43 g). The solid partially crystallized on standing overnight to provide, after collecting and washing with pentane, the title compound, (15.5 g).

Workup

  1. temperaturemaintaining the reaction temperature below 50° C.
  2. additionduring the addition
  3. custompartitioned between dichloromethane (100 ml) and water (100 ml)
  4. customthe layers separated
  5. washThe dichloromethane layer was washed with 5% aqueous sodium sulphite solution (50 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a pale yellow solid, (43 g)
  10. customThe solid partially crystallized
  11. waiton standing overnight
  12. customto provide
  13. customafter collecting
  14. washwashing with pentane

Sources & evidence

ORD record
ord-8a48f48d058047e7b8899c16ce431b80
Source dataset
uspto-grants-1998_02
Patent number
US05714628

Reaction notes

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