Sodium Chloride → 1,4-Dioxaspiro[4.6]undecan-7-ol

HRID 1290085

Reaktionsgleichung

Reaktionsgleichung von HRID 1290085
[O:1]1CCCC1.[CH2:6]1[O:16][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[O:8][CH2:7]1.[BH4-].[Na+].[Cl-].[Na+]>O.[OH-].[Na+].C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH2:7]1[O:8][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([OH:1])[CH2:10]2)[O:16][CH2:6]1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 2794811,4-Dioxaspiro(4.6)undec-6-eneHCID 4311764Sodium borohydride

Produkt 1

HCID 132988111,4-Dioxaspiro[4.6]undecan-7-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 15337Mercuric acetateKatalysatorHCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

Mercury (II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A 10% aqueous sodium hydroxide solution (150 mL) was added, followed by a solution of sodium borohydride (4.8 g, 0.13 mol) in 10% aqueous sodium hydroxide (150 mL). The mixture was allowed to reach ambient temperature and stirred overnight. The mixture was saturated with sodium chloride, stirred for 30 minutes, then allowed to settle; the solution was decanted into brine and extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-Hydroxycycloheptanone ethylene ketal (36 g).

Aufarbeitung

  1. customto give a suspension
  2. temperaturethe mixture was cooled in an ice water bath
  3. customto reach ambient temperature
  4. stirringstirred overnight
  5. stirringstirred for 30 minutes
  6. customthe solution was decanted into brine
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-86d671f6a87041628ef7d260de493a31
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750702

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