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Water → 1,3-Propanediol, 2,2-diethyl-, cyclic sulfite (ester)

HRID 1806969
Notes
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Reaction equation

HRID 1806969 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8284PrenderolHCID 24386Thionyl Chloride

Product 1

HCID 1990741,3-Propanediol, 2,2-diethyl-, cyclic sulfite (ester)Yield 98.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was then extracted with ethyl ether
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-469106b00cf34de2be5b9ac932a130b0
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354444B2

Reaction notes

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