Thionyl Chloride → HCID 88273893, compound

HRID 1499987Notes

Reaction equation

HRID 1499987 reaction equation
[CH3:1][S:2]([CH2:5][CH:6]([OH:9])[CH2:7][OH:8])(=[O:4])=[O:3].[S:10](Cl)(Cl)=[O:11]>C(Cl)Cl>[CH3:1][S:2]([CH2:5][CH:6]1[CH2:7][O:8][S:10](=[O:11])[O:9]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 214129233-(Methanesulfonyl)propane-1,2-diol

Product 1

HCID 88273893HCID 88273893, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

9.00 g (58.4 mmol) of 3-(methylsulfonyl)propane-1,2-diol was dissolved in 100 mL of methylene chloride. 7.64 g (64.2 mmol) of thionyl chloride was dropwise added to the solution at an inner temperature of from 20 to 25° C. After this was stirred at 35° C. for 2 hours, the solvent and the remaining thionyl chloride were evaporated away under reduced pressure to give 11.40 g of a crude crystal. The obtained crude crystal was recrystallized from dimethyl carbonate/2-propanol to give 6.60 g of the intended 4-(methylsulfonylmethyl)-1,3,2-dioxathiolane-2-oxide as a diastereomeric mixture (mixture ratio 9/1) (yield 56%).

Workup

  1. customthe solvent and the remaining thionyl chloride were evaporated away under reduced pressure
  2. customto give 11.40 g of a crude crystal
  3. customThe obtained crude crystal
  4. customwas recrystallized from dimethyl carbonate/2-propanol

Sources & evidence

ORD record
ord-8296b1c8fef4468b8dbbc12fde970379
Source dataset
uspto-grants-2015_12
Patent number
US09203113B2

Reaction notes

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