Sulfuric Acid → ADONA
Reaction equation
[K+].[Br-].[F:3][C:4]([F:24])([CH:7]([F:23])[O:8][C:9]([F:22])([F:21])[C:10]([F:20])([F:19])[C:11]([F:18])([F:17])[O:12][C:13]([F:16])([F:15])[F:14])[CH2:5][OH:6].[O-]Cl.[Na+].S(=O)(=O)(O)[OH:29]>O.CC#N>[F:3][C:4]([F:24])([CH:7]([F:23])[O:8][C:9]([F:22])([F:21])[C:10]([F:19])([F:20])[C:11]([F:17])([F:18])[O:12][C:13]([F:14])([F:15])[F:16])[C:5]([OH:29])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
5.5 mL water, 20 mL MeCN, 0.36 g KBr, 4-MeOTEMPO (0.15 g), and 10 g of 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol are placed in a 50 ml glass flask equipped with a dropping funnel and stirrer. 36 mL of a 15% wt. aq. NaOCl solution buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Concentrated sulphuric acid and water were added to make the reaction mixture acidic (pH 1 to 2). The reaction mixture was extracted three times with diethyl ether. The combined ether phases were dried over magnesium sulphate and the solvent was removed by a rotary evaporator. The residue was distilled to give 8.4 g of the acid (b.p. 58 C, 1.6 mmHg). Yield: 81%.
Workup
- customequipped with a dropping funnel and stirrer
- additionwere added via the dropping funnel in 3 portions over two days
- extractionThe reaction mixture was extracted three times with diethyl ether
- dry with materialThe combined ether phases were dried over magnesium sulphate
- customthe solvent was removed by a rotary evaporator
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-442fc6048e5844748dfaf437fe10e2c8
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809580B2
Reaction notes
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