Cyclooctanol → 1-Chloroethyl cyclooctyl carbonate
Reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10](Cl)(=[O:15])[O:11][CH:12]([Cl:14])[CH3:13]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:10](=[O:15])([O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[O:11][CH:12]([Cl:14])[CH3:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -60 °C
Procedure
To a solution of cyclooctanol (1.79 g) in chloroform (40 mL), pyridine (1.13 mL) was added, and then the reaction solution was cooled to −60° C. To the reaction solution, 1-chloroethyl carbonochloridate (1.53 mL) was added at the same temperature over 10 minutes. The reaction solution was thereafter heated to room temperature and stirred at the same temperature for 3 hours. Chloroform was added to the reaction solution and the organic layer was washed three times with brine and then dried over magnesium sulfate. The insoluble was filtered and the filtrate was concentrated under reduced pressure to give 1-chloroethyl cyclooctyl carbonate (A-11-1, 3.70 g) as a colorless oil.
Workup
- temperatureThe reaction solution was thereafter heated to room temperature
- washthe organic layer was washed three times with brine
- dry with materialdried over magnesium sulfate
- filtrationThe insoluble was filtered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f58b2a1e97c54e9296f5f9a758c02add
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428483B2
Reaction notes
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