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

HRID 1957448Notes

Reaction equation

HRID 1957448 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
  10. customThe solid partially crystallized
  11. waiton standing overnight
  12. customto provide
  13. customafter collecting
  14. washwashing with pentane

Sources & evidence

ORD record
ord-3e5d7ee51b214f77afa366dfe2e2c617
Source dataset
uspto-grants-1998_07
Patent number
USRE035865

Reaction notes

Loading…