Diethyl Ether → HCID 20337429, compound

HRID 1706269Notes

Reaction equation

HRID 1706269 reaction equation
CS(C)(=O)=C.[CH3:6][C:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])=[O:8].[CH3:19]COCC>CS(C)=O.O>[CH3:18][O:17][C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[C:7]1([CH3:19])[O:8][CH2:6]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 709912',5'-DimethoxyacetophenoneHCID 6396768Dimethylsulfoxonium methylide

Product 1

HCID 20337429HCID 20337429, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of dimethylsulfoxonium methylide (69.4 mM) in dimethyl sulfoxide (65 ml.) at room temperature is added solid 2,5-dimethoxyacetophenone (10 g., 55.5 mM). The reaction mixture is stirred for one hour at 25° C., for one-half hour at 50° C. and is then cooled. The mixture is diluted with water (50 ml.) and added to a mixture of ice water (200 ml.)--ether (250 ml.)--low boiling petroleum ether (25 ml.). The organic extract is washed twice with water (250 ml.), dried (MgSO4) and evaporated to an oil. Fractional distillation of the oil yields 2,5-dimethoxy-α-methylstyrene oxide.

Workup

  1. temperatureis then cooled
  2. extractionThe organic extract
  3. washis washed twice with water (250 ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated to an oil
  6. distillationFractional distillation of the oil

Sources & evidence

ORD record
ord-122ee6af287f457baba54c2ac67fb966
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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