Thionyl Chloride → 5,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide
Reaction equation
[S:1](Cl)(Cl)=[O:2].[CH3:5][C:6]([CH3:11])([CH2:9][OH:10])[CH2:7][OH:8]>ClCCl>[CH3:5][C:6]1([CH3:11])[CH2:9][O:10][S:1](=[O:2])[O:8][CH2:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Thionylchloride (735 mL) is added to a solution of 2,2-dimethylpropane-1,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40° C. for 3 hours and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf=0.65 (silicagel, cyclohexane/ethyl acetate 3:1).
Workup
- temperaturechilled in an ice bath
- custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
- washThe organic phase is washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-af424466045b46e7854c08638e34faf0
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642585B2
Reaction notes
Loading…