Diethyl Ether → HCID 86737257, compound

HRID 903201Notes

Reaction equation

HRID 903201 reaction equation
[CH2:1]1[CH2:10][O:9][CH2:8][CH:3]([CH2:4][CH2:5][CH:6]=C)[O:2]1.CC[O:13]CC.I([O-])(=O)(=O)=O.[Na+].I([O-])(=O)(=O)=O>[Os](=O)(=O)(=O)=O.O>[CH2:1]1[CH2:10][O:9][CH2:8][CH:3]([CH2:4][CH2:5][CH:6]=[O:13])[O:2]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 167232PeriodateHCID 23667635Sodium periodateHCID 70372852HCID 70372852, compound

Product 1

HCID 86737257HCID 86737257, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-ethylenedioxy-1-hexene (6.0 g.), osmium tetroxide (0.5 g.) , ether (150 ml.) and water (150 ml.) is treated portionwise with sodium metaperiodate (19.3 g.) so that the reaction temperature does not exceed 30°. After the addition of the periodate, a voluminous white solid precipitates out. The mixture is stirred 2.5 hrs. at room temperature, then filtered, and the solid portion is washed with more aqueous ether. The aqueous portion of the filtrate is separated and extracted with three portions of methylene chloride. The combined organic phases are dried with magnesium sulfate, filtered, and evaporated in vacuo. Distillation of the residue yields 4-ethylenedioxy-pentanal (65% yield) b.p. 56°-58°/10.5 mm nmr (CDCl3)δ: 1.27 (s, CH3), 2.04-2.80 (m, --CH2 --CH2 --); 3.9 (s, --OCH2 --CH2 --O), 9.73 (t, O=C--H). IR (film) μ: 3.66; 3.79.

Workup

  1. customdoes not exceed 30°
  2. customa voluminous white solid precipitates out
  3. filtrationat room temperature, then filtered
  4. washthe solid portion is washed with more aqueous ether
  5. customThe aqueous portion of the filtrate is separated
  6. extractionextracted with three portions of methylene chloride
  7. dry with materialThe combined organic phases are dried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. distillationDistillation of the residue

Sources & evidence

ORD record
ord-050cd6f77ae94d519f392449ebbb8b77
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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