Sodium Iodide → HCID 13368600, compound

HRID 653075Notes

Reaction equation

HRID 653075 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][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=1>C(C(C)=O)C>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:32][C:29]2[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][Br:23])=[CH:27][CH:28]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 201955871-(2-Bromoethyl)-4-(bromomethyl)benzene

Product 1

HCID 13368600HCID 13368600, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 1-(2,4-dihydroxy-3-propylphenyl)ethanone (10.0 g; 0.051 m) in dry methyl ethyl 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 added 4-(2-bromoethyl)phenylmethylbromide (14.2 g; 0.051 m) (literature preparation) and the suspension gently heated at reflux overnight. The cooled suspension was evaporated under reduced pressure, the residue taken up 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 under reduced pressure to give a yellow oil. The oil was chromatographed on a U30 Sorbsil column using dichloromethane to give a pale yellow oil which crystallised on standing to a white crystalline solid; recrystallised from ethanol m.p. 66°-70° C.

Workup

  1. temperaturethe suspension gently heated
  2. temperatureat reflux overnight
  3. customThe cooled suspension was evaporated under reduced pressure
  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 under reduced pressure
  10. customto give a yellow oil
  11. customThe oil was chromatographed on a U30 Sorbsil column
  12. customto give a pale yellow oil which
  13. customcrystallised
  14. customrecrystallised from ethanol m.p. 66°-70° C.

Sources & evidence

ORD record
ord-659d0a4c1d1347409f864f548ffc948e
Source dataset
uspto-grants-1987_06
Patent number
US04675334

Reaction notes

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