Picolyl chloride hydrochloride → [4-(2-Pyridylmethyloxy)phenyl]propan-2-one

HRID 465445Notes

Reaction equation

HRID 465445 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]=[CH:22][C:21]=1[CH2:26]Cl>C(O)C>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:14])[CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 2723922Sodium ethoxideHCID 566304374-Hydroxyphenylpropan-2-one ethylene ketal

Product 1

HCID 19874579[4-(2-Pyridylmethyloxy)phenyl]propan-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (28 g) in ethanol (40 ml) was added to a stirred solution of sodium ethoxide in ethanol (7.1 g of sodium in 100 ml) and the resulting solution stirred at room temperature for 20 minutes. A suspension of 2-picolyl chloride hydrochloride (25 g) in ethanol (60 ml) was added and the resulting mixture was boiled under reflux for 5 hours, cooled and filtered. 2M Hydrochloric acid (100 ml) was added, the solution boiled for 5 h, cooled and neutralised with 2M sodium hydroxide solution. After dilution with water the solution was extracted with dichloromethane and the washed organic phase dried and evaporated to give a dark oil. Bulb to bulb distillation gave [4-(2-pyridylmethyloxy)phenyl]propan-2-one, b.pt. 96°-100° C./0.2 mm, which was used without further purification.

Workup

  1. additionwas added
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. addition2M Hydrochloric acid (100 ml) was added
  6. waitthe solution boiled for 5 h
  7. temperaturecooled and neutralised with 2M sodium hydroxide solution
  8. extractionAfter dilution with water the solution was extracted with dichloromethane
  9. customthe washed organic phase dried
  10. customevaporated
  11. customto give a dark oil
  12. distillationBulb to bulb distillation

Sources & evidence

ORD record
ord-43d8c417b6d04421a39c4f7c1b52fc86
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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