Hydrochloric Acid → 1-(3-Chlorophenyl)-3-methylcyclohexan-1-ol

HRID 1065552

Reaktionsgleichung

Reaktionsgleichung von HRID 1065552
[Mg].Br[C:3]1[CH:4]=[C:5]([Cl:9])[CH:6]=[CH:7][CH:8]=1.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1.Cl>C(OCC)C>[Cl:9][C:5]1[CH:4]=[C:3]([C:13]2([OH:17])[CH2:14][CH2:15][CH2:16][CH:11]([CH3:10])[CH2:12]2)[CH:8]=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 79281-Bromo-3-chlorobenzeneHCID 115673-MethylcyclohexanoneHCID 5462224Magnesium

Produkt 1

HCID 128530471-(3-Chlorophenyl)-3-methylcyclohexan-1-olAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

For example, magnesium turnings (6.4 g, 0.26 mole) were flame-dried, the containing glassware was cooled, and 3-bromochlorobenzene (50 g, 0.26 mole), in 50 ml of diethyl ether was added. As the reaction began, an additional 200 ml of diethyl ether was added, and the reaction mixture was heated under reflux for 0.5 hour. To the refluxing reaction mixture was added dropwise, during a 0.5 hour period, 3-methylcyclohexanone (29.2 g, 0.26 mole) in 100 ml of diethyl ether. Upon complete addition, the reaction mixture was heated under reflux for an additional 0.5 hour, then poured into 500 ml of icewater containing 50 ml of hydrochloric acid. The mixture was extracted with three 200 ml portions of diethyl ether. The combined extract was washed twice with 100 ml portions of an aqueous solution saturated with sodium chloride. After separation, the organic layer was dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to an oil. The oil was purified by distillation using a Kugelrohr distilling system at 85°/0.05 mm for 2.5 hours to give 1-(3-chlorophenyl)-3-methylcyclohexan-1-ol (25 g).

Aufarbeitung

  1. temperaturethe containing glassware was cooled
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 0.5 hour
  4. customTo the refluxing reaction mixture
  5. additionwas added dropwise, during a 0.5 hour period
  6. additionUpon complete addition
  7. temperaturethe reaction mixture was heated
  8. temperatureunder reflux for an additional 0.5 hour
  9. additionpoured into 500 ml of icewater
  10. extractionThe mixture was extracted with three 200 ml portions of diethyl ether
  11. extractionThe combined extract
  12. washwas washed twice with 100 ml portions of an aqueous solution saturated with sodium chloride
  13. customAfter separation
  14. dry with materialthe organic layer was dried over sodium sulfate
  15. filtrationfiltered
  16. customThe filtrate was evaporated under reduced pressure to an oil
  17. distillationThe oil was purified by distillation
  18. distillationdistilling system at 85°/0.05 mm for 2.5 hours

Quellen und Nachweise

ORD-Eintrag
ord-048d5c3480ba4975b8bdc5c3e89259ad
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04329518

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