Thionyl Chloride → 5,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide

Reaktionsgleichung

[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]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

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).

Aufarbeitung

custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
washThe organic phase is washed with brine
dry with materialdried (MgSO4)
customThe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag: ord-a87fc34e87e342288e807e1ddf50ce32
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642585B2

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Komponenten

Edukt 2

HCID 24386Thionyl Chloride

HCID 31344Neopentyl glycol

Produkt 1

HCID 108772945,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel