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

HRID 582833

Reaction equation

HRID 582833 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 15337Mercuric acetateCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-99ce5a5021e44c3c941cb9bb12988d89
Source dataset
uspto-grants-1999_07
Patent number
US05925770

Linked notes

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