Sodium Hydroxide → 1,7,10-Trioxadispiro(2.2.4^(6).2^(3))dodecane

HRID 432601

Reaction equation

HRID 432601 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH3:12]OS([O-])(=O)=O.C[S+](C)C.[OH-].[Na+]>C(Cl)Cl>[O:10]1[C:7]2([CH2:6][CH2:5][C:4]3([O:3][CH2:2][CH2:1][O:11]3)[CH2:9][CH2:8]2)[CH2:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2760871Trimethylsulfonium methyl sulfate

Product 1

HCID 120759531,7,10-Trioxadispiro(2.2.4^(6).2^(3))dodecaneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.00 g (76.83 mmol, 1.0 equiv.) of 1,4 Cyclohexanedione ethylene ketal was added to 120 ml methylene chloride along with 18.8 g (99.88 mmol, 1.3 equiv.) of trimethyl sulfonium methyl sulfate. 40 ml 50% sodium hydroxide (NaOH) was added last and the reaction was refluxed for 24 hours. The methylene chloride was removed, 200 ml ether was added and the ether layer was washed with water. The organic layer was dried with sodium sulfate and concentrated down, leaving a yellow oil, 1,7,10-trioxa-dispiro[2.2.4.2]dodecane. (12.13 g, 93% yield). No further purification was necessary.

Workup

  1. temperaturethe reaction was refluxed for 24 hours
  2. customThe methylene chloride was removed
  3. addition200 ml ether was added
  4. washthe ether layer was washed with water
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-74e1ae7b45ae415898970a1391756682
Source dataset
uspto-grants-2003_12
Patent number
US06664258B1

Linked notes

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