Sodium Iodide → 1-{2-Hydroxy-3-propyl-4-[3-(4-nitrophenoxy)propoxy]phenyl}ethanone

HRID 653071Notes

Reaction equation

HRID 653071 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[C:10]([C:13]([CH3:15])=[O:14])[CH:9]=[CH:8][C:7]=1[OH:16].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29]Cl)=[CH:22][CH:21]=1)([O-:19])=[O:18].[I-].[Na+]>CN(C)C=O>[OH:12][C:11]1[C:6]([CH2:5][CH2:4][CH3:3])=[C:7]([O:16][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[C:13](=[O:14])[CH3:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Product 1

HCID 134581331-{2-Hydroxy-3-propyl-4-[3-(4-nitrophenoxy)propoxy]phenyl}ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To sodium hydride (6.1 g, 50% dispersion) in dry dimethylformamide (200 ml) was added 2,4-dihydroxy-3-propylacetophenone (24.6 g) in dimethylformamide (20 ml), dropwise with stirring under nitrogen. The resulting solution was heated to 100° C. and 4-nitro-1-(3-chloropropoxy)benzene (27.3 g) and sodium iodide (19.0 g) were added rapidly. The reaction mixture was left to stir over night at 100° C., cooled and evaporated under reduced pressure to a brown oil. The oil was taken up in water, extracted with dichloromethane (×2), washed with aqueous sodium hydroxide (2N), then aqueous sodium thiosulphate, dried over magnesium sulphate, filtered and evaporated under reduced pressure to a dark brown solid. The solid was recrystallised from methanol, with charcoaling, to give pale yellow needles of product, m.p. 98° C.

Workup

  1. waitThe reaction mixture was left
  2. stirringto stir over night at 100° C.
  3. temperaturecooled
  4. customevaporated under reduced pressure to a brown oil
  5. extractionextracted with dichloromethane (×2)
  6. washwashed with aqueous sodium hydroxide (2N)
  7. dry with materialaqueous sodium thiosulphate, dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure to a dark brown solid
  10. customThe solid was recrystallised from methanol, with charcoaling
  11. customto give pale yellow needles of product, m.p. 98° C.

Sources & evidence

ORD record
ord-fc81a60a28cc4c5b99e425a6eeabb185
Source dataset
uspto-grants-1987_06
Patent number
US04675333

Reaction notes

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