Hydrochloric Acid → 3-{[1,1'-Bi(cyclopropane)]-2-yl}phenol

HRID 1952893ノート

反応式

HRID 1952893 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23301566HCID 23301566、化合物

生成物 1

HCID 233015643-{[1,1'-Bi(cyclopropane)]-2-yl}phenol収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
250 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0772e06043c54cbdb87f9e3a536fd652
出典データセット
uspto-grants-2000_09
特許番号
US06114375

反応ノート

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