Cyclopentanol → Cyclopentyl methanesulfonate
Reaction equation
C(N(CC)CC)C.[CH:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([O:13][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:17])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
Into a one liter, four-necked, round bottom flask equipped with stirrer, condenser, thermometer, and addition funnel, 25.3 parts of triethylamine, 17.2 parts of cyclopentanol, and 190.0 grams of methylene chloride were mixed under a nitrogen blanket and cooled to -40° C. with a dry ice-acetone bath. To this mixture 26.2 parts of methanesulfonyl chloride were added over one hour. The reaction mixture was stirred at -40° C. for an additional two hours and then allowed to warm to 0° C. and maintained at this temperature for eighteen hours. The mixture was vacuum filtered and then washed successively with chilled dilute sulfuric acid (twice with 200 part-portions), dilute sodium bicarbonate (three times with 200 part-portions), and water (twice with 200 part-portions). Subsequently the mixture was dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield cyclopentyl methanesulfonate.
Workup
- customInto a one liter, four-necked, round bottom flask equipped with stirrer, condenser
- additionthermometer, and addition funnel
- temperatureto warm to 0° C.
- temperaturemaintained at this temperature for eighteen hours
- filtrationfiltered
- washwashed successively
- temperaturewith chilled dilute sulfuric acid (twice with 200 part-portions), dilute sodium bicarbonate (three times with 200 part-portions), and water (twice with 200 part-portions)
- dry with materialSubsequently the mixture was dried over sodium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-fae57300477343538e6a075576906d3e
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04454274
Reaction notes
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