Sodium Sulfite → HCID 86688388, compound

HRID 1748918Notes

Reaction equation

HRID 1748918 reaction equation
[CH:1]12[O:12][CH:4]([CH:5]([S:7]([O:10][CH3:11])(=[O:9])=[O:8])[CH2:6]1)[CH:3]=[CH:2]2.ClC1C=CC=C(C(OO)=[O:21])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O:21]1[C:3]2[CH:4]3[O:12][CH:1]([CH2:6][CH:5]3[S:7]([O:10][CH3:11])(=[O:8])=[O:9])[C:2]1=2

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 20768638Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonate

Product 1

HCID 86688388HCID 86688388, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a four-necked flask having a capacity of 1000 mL and equipped with a stirrer, a dropping funnel, and a thermometer, 22.0 g of methyl 7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate and 450 g of methylene chloride were sequentially added, and the resultant mixture was cooled to 4° C. 22.9 g (0.17 mol) of m-chloroperbenzoic acid was slowly added to the flask under stirring so as to attain a temperature of 10° C. or lower. The resultant mixture was stirred at 5 to 7° C. for 4 hours, and then 100 g of saturated aqueous sodium sulfite solution was added to the mixture, followed by stirring for 30 minutes. The mixture was allowed to stand for liquid-liquid separation, and then washing was carried out thrice with 100 g of saturated aqueous sodium hydrogencarbonate solution. The resultant organic layer was concentrated under reduced pressure, to thereby obtain 20.2 g of methyl 2,3-epoxy-7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate.

Workup

  1. customTo a four-necked flask having
  2. customa capacity of 1000 mL and equipped with a stirrer, a dropping funnel
  3. customa temperature of 10° C.
  4. stirringby stirring for 30 minutes
  5. customto stand for liquid-liquid separation
  6. washwashing
  7. concentrationThe resultant organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92e140ecffe14b5697dc5345357b4bee
Source dataset
uspto-grants-2015_10
Patent number
US09152042B2

Reaction notes

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