Hydrochloric Acid → [4-(3-Pyridylmethyloxy)phenyl]propan-2-one

HRID 465444Notes

Reaction equation

HRID 465444 reaction equation
C1[O:14][C:4]([CH3:13])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)OC1.[O-]CC.[Na+].Cl.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Cl)[CH:21]=1.Cl>C(O)C.CO>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:14])[CH3:13])=[CH:11][CH:10]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 2723922Sodium ethoxideHCID 566304374-Hydroxyphenylpropan-2-one ethylene ketal

Product 1

HCID 19874530[4-(3-Pyridylmethyloxy)phenyl]propan-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 887MethanolSolvent

Procedure

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (5 g) in ethanol (20 ml) was added to a stirred solution of sodium ethoxide in ethanol (1.26 g sodium in 50 ml). A suspension of 3-picolyl chloride hydrochloride (4.5 g) in ethanol (40 ml) was added, the mixture boiled for 41/2 hr, cooled and filtered. After evaporation of the solvent the residue was chromatographed on alumina. Elution with 10% methanol in dichloromethane gave a dark oil which was dissolved in methanol (50 ml) and boiled with 2M hydrochloric acid (40 ml) for 3 hours. Neutralisation with 2M sodium hydroxide solution followed by extraction into dichloromethane yielded an oil which was purified by bulb to bulb distillation at 70° C./0.4 mm to give [4-(3-pyridylmethyloxy)phenyl]propan-2-one.

Workup

  1. additionwas added
  2. custom2 hr
  3. temperaturecooled
  4. filtrationfiltered
  5. customAfter evaporation of the solvent the residue
  6. customwas chromatographed on alumina
  7. washElution with 10% methanol in dichloromethane
  8. customgave a dark oil which
  9. extractionNeutralisation with 2M sodium hydroxide solution followed by extraction into dichloromethane
  10. customyielded an oil which
  11. distillationwas purified by bulb to bulb distillation at 70° C./0.4 mm

Sources & evidence

ORD record
ord-afc9c8ccd5e24fffa1be0406bbb7c355
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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