Potassium Carbonate → 2323-17-3

HRID 656032Notes

Reaction equation

HRID 656032 reaction equation
[CH2:1]=[CH:2][CH2:3][C:4](=[O:8])[CH2:5][CH:6]=[CH2:7].O.O.O.O.O.O.O.O.O.[S-2:18].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH3:7][CH:6]1[CH2:5][C:4](=[O:8])[CH2:3][CH:2]([CH3:1])[S:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73972Sodium sulfide nonahydrateHCID 11423569HCID 11423569, compound

Product 1

HCID 137817942323-17-3Yield 29.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound.

Workup

  1. additionadded to the solution above and
  2. extractionextracted with diethyl ether
  3. washThe combined organics were washed with brine, dried MgSO4
  4. concentrationconcentrated
  5. customThe crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Sources & evidence

ORD record
ord-fe4be615df72486bb7bf41e0587f054d
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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