Sodium Iodide → HCID 13019292, compound

HRID 653074Notes

Reaction equation

HRID 653074 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[Br:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Br)=[CH:27][CH:26]=1>CC(CC)=O.CCOCC>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([CH2:24][Br:23])=[CH:26][CH:27]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 693351,4-Bis(bromomethyl)benzeneHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13019292HCID 13019292, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 1-(2,4-dihydroxy-3-propyl phenyl) ethanone (10.0 g; 0.051 m) in dry methylethyl ketone (100 ml) was added dried anhydrous sodium carbonate (27 g; 5 mol. eq) and sodium iodide (0.5 g). To the stirred suspension was then added α,α'-dibromo-p-xylene (13.5 g; 0.051 m) and the suspension gently heated at reflux for five hours. The cooled suspension was evaporated under reduced pressure, the residue dissolved in water and extracted with dichloromethane (×2). The organic extract was washed with aqueous sodium hydroxide (2N), then water, dried over magnesium sulphate, filtered, and evaporated to dryness under reduced pressure to give a yellow solid. The solid was stirred with ether (200 ml) for 1 hour and filtered to remove any disubstituted impurity. The filtrate was evaporated under reduced pressure to leave a yellow solid. The solid was chromatographed on a U30 Sorbsil solumn using dichloromethane to give a white solid; recrystallised from ethanol, m.p. 98°-99° C.

Workup

  1. temperatureat reflux for five hours
  2. customThe cooled suspension was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with dichloromethane (×2)
  5. extractionThe organic extract
  6. washwas washed with aqueous sodium hydroxide (2N)
  7. dry with materialwater, dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. customto give a yellow solid
  11. filtrationfiltered
  12. customto remove any disubstituted impurity
  13. customThe filtrate was evaporated under reduced pressure
  14. customto leave a yellow solid
  15. customThe solid was chromatographed on a U30 Sorbsil solumn
  16. customto give a white solid
  17. customrecrystallised from ethanol, m.p. 98°-99° C.

Sources & evidence

ORD record
ord-20f1dd02ec214586ae6654f4853d53ff
Source dataset
uspto-grants-1987_06
Patent number
US04675334

Reaction notes

Loading…