Sodium Iodide → HCID 14986374, compound

HRID 1494244Notes

Reaction equation

HRID 1494244 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]=1[O:14][CH3:15].[OH:16][C:17]1[C:22]([CH2:23][CH2:24][CH3:25])=[C:21]([OH:26])[CH:20]=[CH:19][C:18]=1[C:27](=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[OH:16][C:17]1[C:22]([CH2:23][CH2:24][CH3:25])=[C:21]([O:26][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]=2[O:14][CH3:15])[CH:20]=[CH:19][C:18]=1[C:27](=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 14986373HCID 14986373, compound

Product 1

HCID 14986374HCID 14986374, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.36 g (15.9 mmol) of 1-(4-bromobutyl)-2,3-dimethoxybenzene, 3.10 g (15.9 mmol) of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 4.4 g (32 mmol) of potassium carbonate and 2.4 g (16 mmol) of sodium iodide in 100 mL of acetone was stirred at reflux for 30 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by high pressure liquid chromatography using 20% ethyl acetate-hexane gave 5.07 g (88% yield) of 1-[2-Hydroxy-4-[4-(2,3-dimethoxyphenyl)butoxy]-3-propylphenyl]-ethanone as an oil.

Workup

  1. temperatureat reflux for 30 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customPurification by high pressure liquid chromatography

Sources & evidence

ORD record
ord-1dd4ab232f324cd5aeb7bb7c4445a958
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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