Hydrochloric Acid → Cyclopropyl 3-methylphenyl ketone

HRID 436930

反応式

HRID 436930 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.Cl>CCOCC.[Cl-].[Cd+2].[Cl-]>[C:4]1([CH3:8])[CH:5]=[CH:6][CH:7]=[C:2]([C:13]([CH:10]2[CH2:12][CH2:11]2)=[O:14])[CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 115603-BromotolueneHCID 77637Cyclopropanecarbonyl chlorideHCID 5462224Magnesium

生成物 1

HCID 21431776Cyclopropyl 3-methylphenyl ketone

試薬・触媒・溶媒 2

HCID 24633Cadmium chloride, dihydrate触媒HCID 3283Diethyl Ether溶媒3 回

実験手順

m-Bromotoluene (34.2 g) in dry ether (120 ml) was added dropwise to magnesium turnings (4.8 g) in dry ether (100 ml). The heat of reaction maintained the mixture to boiling under reflux during the addition and the mixture was heated under reflux for a further hour. The mixture was cooled to 0°, dry cadmium chloride (19.6 g) was added and the temperature allowed to rise to 20° C. After 1 hour, cyclopropanecarbonyl chloride (20.8 g) in dry ether (50 ml) was added dropwise and the mixture was heated under reflux for 4 hours, cooled to 0° and treated with 2 N hydrochloric acid. The ether layer was separated, washed with aqueous sodium bicarbonate (3× 100 ml., 8%) and with water, dried over magnesium sulphate, filtered and evaporated. The residue was distilled under reduced pressure and the fraction b.p. 86°-90°/0.4 mm was collected.

後処理

  1. temperatureThe heat of reaction
  2. temperaturemaintained the mixture
  3. temperatureunder reflux during the addition
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further hour
  6. temperatureThe mixture was cooled to 0°
  7. customto rise to 20° C
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for 4 hours
  10. temperaturecooled to 0°
  11. customThe ether layer was separated
  12. washwashed with aqueous sodium bicarbonate (3× 100 ml., 8%) and with water
  13. dry with materialdried over magnesium sulphate
  14. filtrationfiltered
  15. customevaporated
  16. distillationThe residue was distilled under reduced pressure
  17. customthe fraction b.p. 86°-90°/0.4 mm was collected

出典と根拠

ORDレコード
ord-7b929bf6353d419388452c021da36ff0
出典データセット
uspto-grants-1977_06
特許番号
US04028404

関連ノート

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