Water → 1,3-Propanediol, 2,2-diethyl-, cyclic sulfite (ester)
Reaction equation
[CH2:1]([C:3]([CH2:8][CH3:9])([CH2:6][OH:7])[CH2:4][OH:5])[CH3:2].[S:10](Cl)(Cl)=[O:11].O>C(OCC)C>[CH2:1]([C:3]1([CH2:8][CH3:9])[CH2:6][O:7][S:10](=[O:11])[O:5][CH2:4]1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Step A A mixture of 2,2-diethyl-propane-1,3-diol (Aldrich) (5.5 g, 40 mmol) in anhydrous ethyl ether (100 mL) at 0° C. was added thionyl chloride (10.6 g, 90 mmol). The reaction mixture was stirred at 0° C. for 2 h. Water was added. The organic layer was separated, the aqueous layer was then extracted with ethyl ether. The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, concentrated to give 5,5-diethyl-[1,3,2]dioxathiane 2-oxide as a colorless oil (7 g, 98%).
Workup
- customThe organic layer was separated
- extractionthe aqueous layer was then extracted with ethyl ether
- washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-469106b00cf34de2be5b9ac932a130b0
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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