Isopropanol → 8-Hydroxy-6-oxo-octanoic acid methyl ester
Reaction equation
Cl[O-].[Na+].[CH3:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:15])[CH2:12][CH2:13][OH:14].C(O)(C)C>C(O)(=O)C>[CH3:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:15])[CH2:12][CH2:13][OH:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
100 ml of aqueous sodium hypochlorite solution (10-13% active chlorine) were added dropwise at room temperature, over a period of 45 minutes, to 16.6 g (87 mmol) of 6,8-dihydroxyoctanoic acid methyl ester in 200 ml of glacial acetic acid. After stirring for a further 3 hours at room temperature, 180 ml of isopropanol were added in order to destroy excess sodium hypochlorite, and stirring was carried out for 10 minutes. The reaction mixture was then added to 1200 ml of water and extracted several times with methylene chloride. The combined organic phases were washed with cold-saturated sodium hydrogen carbonate solution. After drying over sodium sulfate, the solvent was distilled off using a rotary evaporator. 13.0 g (80%) of 8-hydroxy-6-oxo-octanoic acid methyl ester were obtained.
Workup
- customto destroy excess sodium hypochlorite
- stirringstirring
- waitwas carried out for 10 minutes
- additionThe reaction mixture was then added to 1200 ml of water
- extractionextracted several times with methylene chloride
- washThe combined organic phases were washed with cold-saturated sodium hydrogen carbonate solution
- dry with materialAfter drying over sodium sulfate
- distillationthe solvent was distilled off
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-5e1eb68fcf904fbb9bbf7f375608a741
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06965029B2
Reaction notes
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