Hydrochloric Acid → HCID 59299847, compound

HRID 2236551Notes

Reaction equation

HRID 2236551 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[I-].[Na+].Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.Cl.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:11][C:4]1[CH:3]=[C:2]([O:1][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:7]=[CH:6][C:5]=1[C:8](=[O:10])[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 701334-Hydroxy-2-methylacetophenoneHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 59299847HCID 59299847, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-(4-hydroxy-2-methyl-phenyl)-ethanone (15.0 g, 0.10 mole), sodium iodide (15.0 g, 0.10 mole), 4-(2-chloro-ethyl)-morpholine; hydrochloride (18.6 g, 0.10 mole), anhydrous powdered potassium carbonate (67.0 g, 0.50 mole) and 2-butanone (500 mL) is stirred and heated at a gentle reflux overnight. The mixture is cooled to room temperature, filtered, the solids washed with acetone. The combined filtrates were evaporated in-vacuo, the residue treated with water and extracted with ether. The ether layer is washed with 1N sodium hydroxide, water, brine, dried over anhydrous sodium sulfate, filtered and evaporated to give an oil, 19.2 g. (73%) used as is for the next step.

Workup

  1. temperatureheated at
  2. temperaturea gentle reflux overnight
  3. filtrationfiltered
  4. washthe solids washed with acetone
  5. customThe combined filtrates were evaporated in-vacuo
  6. additionthe residue treated with water
  7. extractionextracted with ether
  8. washThe ether layer is washed with 1N sodium hydroxide, water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto give an oil, 19.2 g

Sources & evidence

ORD record
ord-710ef760eb13475a92485e0eed7fea7d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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