Sodium Iodide → HCID 20230513, compound

HRID 2290806Notes

Reaction equation

HRID 2290806 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([CH2:33]C(=O)C)(=[O:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:31][C:30](=[O:32])[CH3:33])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 15086653HCID 15086653, compound

Product 1

HCID 20230513HCID 20230513, compoundYield 6.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.5 g of 6-(3,4-dibenzyloxyphenyl)hexyl bromide, 0.12 g of acetylacetone, 0.15 g of potassium carbonate, 0.02 g of sodium iodide, and 5 ml of ethanol was refluxed for 20 hours. To the reaction mixture was added 15 ml of water and the product was extracted with 20 ml of ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide a sticky product. The product was applied to silica gel (45 ml) column chromatography and eluted with a mixture of toluene and ethyl acetate (30:1) to provide 33 mg of 9-(3,4-dibenzyloxyphenyl)-2-nonanone as an oil.

Workup

  1. temperaturewas refluxed for 20 hours
  2. extractionthe product was extracted with 20 ml of ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a sticky product
  7. washeluted with a mixture of toluene and ethyl acetate (30:1)

Sources & evidence

ORD record
ord-c4efc53cf10a46ebbc0069927dd46972
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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