Sulfuric Acid → 3(2H)-Furanone, dihydro-2,5-diethyl-2,5-dimethyl-

HRID 341669Notes

Reaction equation

HRID 341669 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][C:7]([OH:17])([C:10]#[C:11][C:12]([CH3:16])(O)[CH2:13][CH3:14])[CH2:8][CH3:9]>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.O>[CH2:8]([C:7]1([CH3:6])[C:10](=[O:2])[CH2:11][C:12]([CH2:13][CH3:14])([CH3:16])[O:17]1)[CH3:9]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 65463,6-Dimethyl-4-octyne-3,6-diol

Product 1

HCID 288773(2H)-Furanone, dihydro-2,5-diethyl-2,5-dimethyl-Yield 435.1%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of mercury (II) acetate (2.7 g, 0.0084 mol), sulfuric acid (2.7 ml, 0.027 mol), water (270 ml) and 3,6-dimethyl-oct-4-yne-3,6-diol (27.0 g, 0.159 mol) is heated at 80° C. The reaction mixture is maintained at 80° C. for 4 hours and allowed to cool to ambient temperature. The mixture is extracted with diethyl ether (3×150 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 2,5-diethyl-2,5-di-methyldihydrofuran-3-one (20 g) as a colourless oil.

Workup

  1. temperatureThe reaction mixture is maintained at 80° C. for 4 hours
  2. temperatureto cool to ambient temperature
  3. extractionThe mixture is extracted with diethyl ether (3×150 ml)
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-73bcf5a311c34779b8bbb4d7de25a052
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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