Sodium Sulfite → HCID 86688388, compound

HRID 1755496Notes

Reaction equation

HRID 1755496 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

Conditions

Temperature
4 °C

Procedure

A four-neck flask having an internal capacity of 1,000 mL and fitted with a stirrer, a dropping funnel and a thermometer was charged sequentially with 22.0 g of methyl 7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate and 450 g of methylene chloride, the temperature was cooled to 4° C., and 22.9 g (0.17 mol) of m-chloroperbenzoic acid was added gradually to the flask under constant stirring so that the temperature did not exceed 10° C. Following stirring for 4 hours at 5 to 7° C., 100 g of a saturated aqueous solution of sodium sulfite was added, and the resulting mixture was stirred for 30 minutes. After standing and separating, the organic layer was washed three times with 100 g samples of saturated sodium hydrogen carbonate. The organic layer was then concentrated under reduced pressure, yielding 20.2 g of methyl 2,3-epoxy-7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate.

Workup

  1. customA four-neck flask having
  2. customan internal capacity of 1,000 mL and fitted with a stirrer, a dropping funnel
  3. customdid not exceed 10° C
  4. stirringFollowing stirring for 4 hours at 5 to 7° C.
  5. stirringthe resulting mixture was stirred for 30 minutes
  6. customseparating
  7. washthe organic layer was washed three times with 100 g samples of saturated sodium hydrogen carbonate
  8. concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b4550901d8c4587853a915cc013ee38
Source dataset
uspto-grants-2015_10
Patent number
US09170487B2

Reaction notes

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