Thionyl Chloride → 5,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide
Reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[S:8](Cl)(Cl)=[O:9]>ClCCl>[CH3:1][C:2]1([CH3:7])[CH2:5][O:6][S:8](=[O:9])[O:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 2,2-dimethyl-propane-1,3-diol (1 g) in dichloromethane (5 mL) is added dropwise at 0° C. thionylchloride (735 μL). The mixture is stirred for 3 hours at 40° C. and then partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated to give the title compound. Yield: 1 g; TLC: rf=0.65 (silicagel, cyclohexane/ethyl acetate 3:1).
Workup
- custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
- washThe organic phase is washed with brine
- dry with materialdried (MgSO4)
- customThe solvent is evaporated
Sources & evidence
- ORD record
- ord-a87fc34e87e342288e807e1ddf50ce32
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642585B2
Reaction notes
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