Sodium Iodide → HCID 53730456, compound

HRID 344930Notes

Reaction equation

HRID 344930 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22]Cl)[CH:5]=1)[CH:2]=[CH2:3].[I-].[Na+].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 54020347HCID 54020347, compound

Product 1

HCID 53730456HCID 53730456, compound

Procedure

A mixture was prepared by mixing 0.5 g of 4-allyl-2-[5allyl-2-(2-chloroethoxy)phenyl]phenol and 1.5 g of sodium iodide with 20 ml of acetonitryl. The mixture was refluxed by heating for 4 hours with stirring, 1 ml of diethylamine was added thereinto, refluxed for 3 hours with stirring and concentrated. The concentrate, wherein water solution of sodium hydrogencarbonate was added, was extracted with chloroform, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (dichloromethane:methanol=30:1) to yield 0.3 g of 4-allyl-2-{5-allyl-2-[2- (N, N-diethyl-amino)ethoxy]phenyl}phenol.

Workup

  1. customA mixture was prepared
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 4 hours
  4. temperaturerefluxed for 3 hours
  5. stirringwith stirring
  6. concentrationconcentrated
  7. additionThe concentrate, wherein water solution of sodium hydrogencarbonate was added
  8. extractionwas extracted with chloroform
  9. dry with materialdried with sodium sulfate
  10. concentrationconcentrated
  11. customThe concentrate was purified by a silica gel column-chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-0e6d6fbc77d64147a2cd17bdaf2d1395
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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