Hydrochloric Acid → Cyclopropyl 3-methylphenyl ketone

HRID 436930

반응식

HRID 436930 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 21431776Cyclopropyl 3-methylphenyl ketone

시약·촉매·용매 2

HCID 24633Cadmium chloride, dihydrate촉매HCID 3283Diethyl Ether용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b929bf6353d419388452c021da36ff0
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04028404

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