Sodium Hydroxide → 4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane

HRID 2051369Notes

Reaction equation

HRID 2051369 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:13])[CH:9]([CH3:10])[CH2:8][CH2:7][CH:6]([CH3:11])[C:5]1=[O:12].[Cl-].[CH3:15][S+](C)C>CS(C)=O>[CH3:13][C:4]1([CH3:3])[CH:9]([CH3:10])[CH2:8][CH2:7][CH:6]([CH3:11])[C:5]21[O:12][CH2:15]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 51304442,2,3,6-TetramethylcyclohexanoneHCID 10176118Trimethylsulfonium chloride

Product 1

HCID 187910594,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

According to a preferred embodiment of the invention, NaOH is added to a mixture consisting of 2,2,3,6-tetramethyl-1-cyclohexanone and trimethylsulfonium chloride in dimethylsulfoxide. The reaction is slightly exothermic, hence the necessity to maintain an external cooling of the reaction mixture so as to keep the temperature at about 25°-30° C. Good stirring is also applied for about 6 hr. 4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane is then obtained by extraction of the resulting mixture with petrol ether, concentration of the organic extracts and fractional distillation.

Workup

  1. additionis added to a mixture
  2. temperaturehence the necessity to maintain
  3. temperaturean external cooling of the reaction mixture so as
  4. customat about 25°-30° C

Sources & evidence

ORD record
ord-f85b611f44f54e56bd406f3464041f72
Source dataset
uspto-grants-1991_05
Patent number
US05017711

Reaction notes

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