Carbon Dioxide → 1,2-Epoxycyclooctane

HRID 1641601

Reaction equation

HRID 1641601 reaction equation
ON1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=O.[CH:9]1[CH2:16]CCCC[CH2:11][CH:10]=1.C(=O)=O.O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH:11]12[O:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:16][CH2:9][CH2:10]2

Participants

7

Conditions

Temperature
40 °C

Procedure

This reaction was performed with a solution of 0.1191 g (1.03 mmol) of N-hydroxysuccinimide, 2.0868 g (18.9 mmol) of cyclooctene and 0.1330 g (0.53 mmol) of cobalt acetate tetrahydrate in 40 ml of acetic acid was heated to 40° C. in a Parr Hastelloy reactor with temperature and pressure transducer. After the temperature reached 40° C., 745 psi of CO2 was introduced into the reactor, then 120 psi of O2 was added slowly to the reactor. The mixture was stirred under pressure for six hours at 40° C., then the pressure was released, and the mixture was cooled to room temperature. The mixture solution was extracted with ethyl acetate then washed with a saturated NaCl solution in water and, dried over Na2SO4 to give cyclooctene oxide, the only product 5% with 5% conversion analyzed by GC-MS.

Workup

  1. customreached 40° C.
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe mixture solution was extracted with ethyl acetate
  4. washthen washed with a saturated NaCl solution in water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-653324f7d9c34be8ad5626145129591c
Source dataset
uspto-grants-2012_02
Patent number
US08115029B2

Linked notes

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