Potassium Carbonate → HCID 67916683, compound

HRID 846224Notes

Reaction equation

HRID 846224 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=1.[CH3:22][CH2:23][CH2:24][C:25]1[C:30]([OH:31])=[C:29]([C:32]([CH3:34])=[O:33])[CH:28]=[CH:27][C:26]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([O:35][CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=2)=[C:25]([CH2:24][CH2:23][CH3:22])[C:30]=1[OH:31])(=[O:33])[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 19884817HCID 19884817, compound

Product 1

HCID 67916683HCID 67916683, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The compound of Step A above, (2.0 g, 5.36 mmoles), 2,4-dihydroxy-3-propylacetophenone (2.08 g, 10.72 mmole) and potassium carbonate (3.0 g, 21.44 mmole) were stirred in methyl ethyl ketone (100 ml) and heated at reflux for three hours. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in ether-methanol and extracted with 1N NaOH (3×50 ml). The organics were dried and concentrated in vacuo. The residue was triturated with methanol, filtered and dried, to yield the title compound. NMR (CDCl3): 0.94 (3H, m), 1.73 (6H, m), 2.28 (6H, m), 2.95 (2H, m), 3.22 (2H, m), 3.66 (3H, s), 4.17 (2H, m), 6.42 (1H, d), 7.40 (2M, d), 7.61 (1H, d), 7.90 (2H, d), 12.73 (1H, s).

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ether-methanol
  6. extractionextracted with 1N NaOH (3×50 ml)
  7. customThe organics were dried
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with methanol
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-3b9eacfe17b343ed955f0e15fc33efca
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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