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

HRID 374340Notes

Reaction equation

HRID 374340 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1([C:17]([O:19]CC)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].OO>C(O)(C)(C)C>[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1([C:17]([OH:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 516892Sodium Bicarbonate2×HCID 19067478HCID 19067478, compound

Product 1

HCID 11010130t-Butyl 3-(1-carboxycyclopentyl)propanoateYield 44.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 2-[2-(tert-butoxycarbonyl)ethyl]-2-ethoxycarbonylcyclohexanone (see Preparation 10) (1.0 g, 3.35 mmol) and sodium hydrogen carbonate (0.281 g, 3.35 mmol) in tert-butanol (2.0 ml) was added, in four portions over a period of 1.5 hours, a 30% aqueous solution of hydrogen peroxide (4×0.11 ml, 4.0 mmol) at 40° C. The mixture was stirred at 40° C. for 20 hours. A fifth charge of a 30% aqueous solution of hydrogen peroxide (0.11 ml) and a further quantity of sodium hydrogen carbonate (0.281 g, 33.5 mmol) was added, and the mixture stirred at 40° C. for 8 hours. The mixture was partitioned between hexane (40 ml) and 5% aqueous sodium sulphite solution (25 ml) and the layers separated. The hexane layer was washed with dilute aqueous ammonia solution (25 ml of 0.880 ammonia in 200 ml of distilled water, 5×40 ml). The combined aqueous extracts were acidified to pH 2-3 with 5.ON aqueous hydrochloric acid solution and extracted with dichloromethane (3×25 ml). The combined dichloromethane extracts were washed with distilled water (25 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as an oil, (0.362 g, 44.6%). Rf. 0.29 (silica, hexane/ethyl acetate 2:1). Analysis %: Found: C, 64.78; H, 9.39; C1H22O4 requires: C, 64.44; H, 9.15.

Workup

  1. additionwas added, in four portions over a period of 1.5 hours
  2. customat 40° C
  3. stirringthe mixture stirred at 40° C. for 8 hours
  4. customThe mixture was partitioned between hexane (40 ml) and 5% aqueous sodium sulphite solution (25 ml)
  5. customthe layers separated
  6. washThe hexane layer was washed with dilute aqueous ammonia solution (25 ml of 0.880 ammonia in 200 ml of distilled water, 5×40 ml)
  7. extractionextracted with dichloromethane (3×25 ml)
  8. washThe combined dichloromethane extracts were washed with distilled water (25 ml)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e48f400afff1430f83252afc3015a781
Source dataset
uspto-grants-1992_11
Patent number
US05166406

Reaction notes

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