Dichloromethane → 3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-8-one

HRID 2181263

Reaction equation

HRID 2181263 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[CH3:9][C:10]([CH3:15])([CH2:13]O)[CH2:11][OH:12].C(Cl)Cl.[OH-].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:9][C:10]1([CH3:15])[CH2:11][O:12][C:3]2([CH2:4][CH2:5][CH2:6][C:1](=[O:8])[CH2:2]2)[O:7][CH2:13]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 104341,3-CyclohexanedioneHCID 14798Sodium HydroxideHCID 31344Neopentyl glycol

Product 1

HCID 153447493,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-8-oneYield 50%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

448.5 g 1,3-cyclohexanedione, 416 g 2,2-dimethyl-1,3-propanediol and 12 g p-toluenesulfonic acid were introduced into 3,000 ml methylene chloride and the mixture was heated under reflux for 24 hours using a water separator. When the reaction had ended the mixture was cooled to room temperature and 2,000 ml 32% sodium hydroxide solution were added. The phases were separated and the organic phase was washed first with sodium bicarbonate solution (44.4 g sodium bicarbonate solution/850 ml water) and then with 350 ml water. The organic phase was dried over sodium sulfate and the solvent was then evaporated in vacuo. 345 g (50% of theory) 3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-8-one were obtained in this way.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customThe phases were separated
  4. washthe organic phase was washed first with sodium bicarbonate solution (44.4 g sodium bicarbonate solution/850 ml water)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was then evaporated in vacuo

Sources & evidence

ORD record
ord-f11a7298898f405b8052c69046015030
Source dataset
uspto-grants-2005_05
Patent number
US06890959B2

Linked notes

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