Oxygen → ADONA
Reaction equation
N([O-])=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.CC(O[Na])=[O:18].[F:21][C:22]([F:42])([CH:25]([F:41])[O:26][C:27]([F:40])([F:39])[C:28]([F:38])([F:37])[C:29]([F:36])([F:35])[O:30][C:31]([F:34])([F:33])[F:32])[CH2:23][OH:24].O=O>C(O)(=O)C>[F:21][C:22]([F:42])([CH:25]([F:41])[O:26][C:27]([F:40])([F:39])[C:28]([F:37])([F:38])[C:29]([F:35])([F:36])[O:30][C:31]([F:32])([F:33])[F:34])[C:23]([OH:18])=[O:24]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
150 mL of acetic acid, 0.91 g sodium nitrite, TEMPO (0.68 g), CH3CO2Na (3.78 g) and 20 g of 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol were placed in a 500 mL glass flask equipped with a reflux condenser, a stirrer and a balloon filled with oxygen which was released into the flask by opening a valve such that the reaction was carried out in an oxygen atmosphere. The mixture was stirred 16 hr at 60° C. Then the mixture was acidified and extracted by diethyl ether (three times). The combined organic phases were washed by water and dried over magnesium sulphate. The solvent was removed at a rotary evaporator and the residue was distilled to give 14.15 g of acid (1.6 mmHg, 58° C.). Yield: 68%.
Workup
- customequipped with a reflux condenser, a stirrer
- extractionextracted by diethyl ether (three times)
- washThe combined organic phases were washed by water
- dry with materialdried over magnesium sulphate
- customThe solvent was removed at a rotary evaporator
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-d8cc6577a693436ba0a445495a0ef706
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809580B2
Reaction notes
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