Hydrochloric Acid → 228267-53-6

HRID 1952893Notes

Reaction equation

HRID 1952893 reaction equation
[CH:1]1([C:4]2[CH2:8][CH:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=3)NN=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O>[CH:1]1([CH:4]2[CH2:8][CH:7]2[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23301566HCID 23301566, compound

Product 1

HCID 23301564228267-53-6Yield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

To a 250 ml round bottom flask equipped with nitrogen inlet, thermometer, and reflux condenser was charged 5.0 g (0.0247 moles) of 3-cyclopropyl-5-(3-hydroxyphenyl)-2-pyrazoline, and 5.0 g of powdered sodium hydroxide (0.125 moles). The two solids were mixed thoroughly, then heated slowly to 250° C., under a rapid stream of nitrogen. The reaction mixture was heated continuously at 250° C. for a total of 2 hours, then cooled to ambient temperature. The resulting residue was the dissolved in 200 mls of water, then acidified to pH 2 with 1 N aqueous hydrochloric acid. The acidic solution was extracted with 3×100 mls of ethyl ether, and the ether extract was washed with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution. The ether extract was the dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure with a rotary evaporator at 45° C. The resulting crude product was chromatographed on silica gel with a 15% ethyl acetate, 85% hexane mobile phase. The pure fractions were combined and concentrated under reduced pressure on a rotary evaporator to afford 2.9 g of the title compound 1-(3-hydroxyphenyl)-2-cyclopropyl cyclopropane as a pale yellow liquid at a 68% yield.

Workup

  1. customTo a 250 ml round bottom flask equipped with nitrogen inlet
  2. temperaturethermometer, and reflux condenser
  3. additionThe two solids were mixed thoroughly
  4. temperatureThe reaction mixture was heated continuously at 250° C. for a total of 2 hours
  5. temperaturecooled to ambient temperature
  6. extractionThe acidic solution was extracted with 3×100 mls of ethyl ether
  7. extractionthe ether extract
  8. washwas washed with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution
  9. extractionThe ether extract
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure with a rotary evaporator at 45° C
  13. customThe resulting crude product was chromatographed on silica gel with a 15% ethyl acetate, 85% hexane mobile phase
  14. concentrationconcentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-0772e06043c54cbdb87f9e3a536fd652
Source dataset
uspto-grants-2000_09
Patent number
US06114375

Reaction notes

Loading…