Dimethyl Sulfide → 4,8,8-Trimethyl-1-oxaspiro[2.5]oct-4-ene

HRID 892666Notes

Reaction equation

HRID 892666 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1.[CH3:11]OS(OC)(=O)=O.S(C)C.[OH-].[Na+]>CS(C)=O>[CH3:1][C:2]1[C:3]2([C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1)[O:10][CH2:11]2

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 883322,6,6-Trimethyl-2-cyclohexen-1-one

Product 1

HCID 117687714,8,8-Trimethyl-1-oxaspiro[2.5]oct-4-eneYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared under the conditions described in a., starting from 25.0 g (181 mmol) of 2,6,6-trimethyl-2-cyclohexen-1-one, 31.9 g (253 mmol) of (CH3)2SO4, 17.0 g (274 mmol) of (CH3)2S and 43.0 g (1086 mmol) of NaOH in 60 ml of DMSO. 22.09 G of the desired product, 91% pure, were obtained.

Workup

  1. customPrepared under the conditions

Sources & evidence

ORD record
ord-6e174837e8974c6b9cde3b4b240f3875
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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