Hydrochloric Acid → HCID 22666462, compound

HRID 1007936Notes

Reaction equation

HRID 1007936 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:18]C)=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[CH3:2].Cl.C(Cl)(Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 22666305HCID 22666305, compound

Product 1

HCID 22666462HCID 22666462, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 5.0 mL of ethyl acetate is dissolved 1.20 g of 1-(5-{2-[2-(diethylamino)ethoxy]ethyl}-2-methoxyphenyl)-1-ethanone, to which is added 1.1 mL of 3.7 mol/L solution of dry hydrogen chloride in ethyl acetate. The solvent is distilled off under reduced pressure. The residue is dissolved in 6.0 mL of methylene chloride, to which are successively added at an ice-cooled temperature 1.60 g of aluminum chloride and 0.70 g of sodium iodide. The mixture thus obtained is stirred at ambient temperature for 2 hours. Ice water and chloroform are added to the reaction mixture, pH is adjusted to 8.0 with 1.0 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is dried over anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Thus, 1.10 g of 1-(5-{2-[2-(diethylamino)ethoxy]ethyl}-2-hydroxyphenyl)-1-ethanone is obtained as an oily product.

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. dissolutionThe residue is dissolved in 6.0 mL of methylene chloride, to which
  3. additionare successively added at an ice-
  4. temperaturecooled temperature 1.60 g of aluminum chloride and 0.70 g of sodium iodide
  5. customThe mixture thus obtained
  6. customthe organic layer is separated
  7. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-d8dabf5e8d19451088c304cae5725b67
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

Loading…