m-Chloroperbenzoic acid → HCID 19885320, compound

HRID 846266Notes

Reaction equation

HRID 846266 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]=[C:13]([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH:19]=[CH2:20]>C(Cl)(Cl)Cl>[CH2:18]([O:17][CH2:16][CH2:15][CH2:14][C:13](=[O:12])[CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[CH:19]1[O:9][CH2:20]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19885323HCID 19885323, compound

Product 1

HCID 19885320HCID 19885320, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 1000-ml round bottom flask equipped with a magnetic stirrer and a dropping funnel was charged with 130 g (0.38 mol) of 50-% m-chloroperbenzoic acid and 450 ml of chloroform. The dropping funnel was charged with 36.10 g (0.18 mol) of allyl 4,7-dioxooctyl ether. The contents of the dropping funnel were added drop-wise to the flask within 1 hour. During the addition the contents of the flask were stirred and kept at about 0° C. by cooling with an external cooling bath. After additional stirring overnight, during which the mixture was allowed to adopt room temperature, the mixture was filtered. The filtrate was extracted with an equal volume of 10-% aqueous sodium hydroxide and with an equal volume of water, dried over magnesium sulphate and evaporated to dryness, leaving 30.4 g of 4,7-dioxooctyl glycidyl ether as a colourless oil. The structure was confirmed by 1H-NMR spectroscopy. The signals were assigned to the underlined hydrogen atoms (shifts relative to TMS, chloroform-d1 solvent): ##STR9##

Workup

  1. customA 1000-ml round bottom flask equipped with a magnetic stirrer and a dropping funnel
  2. additionThe contents of the dropping funnel were added drop-wise to the flask within 1 hour
  3. additionDuring the addition the contents of the flask
  4. customkept at about 0° C.
  5. temperatureby cooling with an external cooling bath
  6. stirringAfter additional stirring overnight, during which the mixture
  7. customto adopt room temperature
  8. filtrationthe mixture was filtered
  9. extractionThe filtrate was extracted with an equal volume of 10-% aqueous sodium hydroxide and with an equal volume of water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-097382cd59a74f1eaae55cf20432f9e1
Source dataset
uspto-grants-1992_08
Patent number
US05135976

Reaction notes

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