Potassium Iodide → HCID 2300059, compound

HRID 1938632Notes

Reaction equation

HRID 1938632 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].[I-].[K+]>O>[CH2:21]([N:23]([CH2:24][CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1)[CH3:22]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 21469848HCID 21469848, compound

Product 1

HCID 2300059HCID 2300059, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-(4-chlorobutoxy)benzophenone (740 g, 1.59 mol), diethylamine (3.7 L), and potassium iodide (50 g) in water (3.7 L). Heat to reflux. After 19 hours, evaporate the reaction mixture in vacuo to give an aqueous residue. Extract two times with ethyl acetate. Extract the combined organic layers with aqueous 10% hydrochloric acid solution and separate the acidic aqueous layer. Combine the acidic aqueous layer and ethyl acetate. Slowly add aqueous 10% sodium hydroxide solution until the pH of the aqueous layer is about 9. Separate the organic layer, extract twice with water and then aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 4-(4-diethylaminobutoxy)benzophenone.

Workup

  1. temperatureHeat to reflux
  2. customevaporate the reaction mixture in vacuo
  3. customto give an aqueous residue
  4. extractionExtract two times with ethyl acetate
  5. extractionExtract the combined organic layers with aqueous 10% hydrochloric acid solution
  6. customseparate the acidic aqueous layer
  7. customSeparate the organic layer
  8. extractionextract twice with water
  9. dry with materialDry the organic layer over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo

Sources & evidence

ORD record
ord-7ba3587fe33e4dc6894c57594721eb97
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

Loading…