Hydrochloric Acid → 5-Cyclopentylidene-2-methylpentan-2-ol

HRID 2187328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187328
[C:1]1(=[CH:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:12][Mg]Br.Cl>CCOCC>[C:1]1(=[CH:6][CH2:7][CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 135280135-Cyclopentylidenepentan-2-oneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 184338645-Cyclopentylidene-2-methylpentan-2-olAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

5-Cyclopentylidene-2-pentanone (13.4 g; 88 mmol) in ether (13 ml) was added dropwise during 30 minutes to a 3M solution of methylmagnesium bromide in ether (38 ml; 114 mmol). After addition of more ether (25 ml), the mixture was heated under reflux for 2 hours, then cooled down to room temperature, poured into ice (40 g), acidified with 5N HCl (50 ml) and extracted with MTBE (130 ml). The aqueous phase was separated and extracted with MTBE (2×130 ml). The combined organic phases were washed with saturated NaHCO3 (2×130 ml), water (130 ml), dried over MgSO4 and concentrated in vacuo. Distillation (52° C.-55° C./0.06 torr) yielded 11.24 g (76% yield) of 5-cyclopentylidene-2-methylpentan-2-ol.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with MTBE (130 ml)
  4. customThe aqueous phase was separated
  5. extractionextracted with MTBE (2×130 ml)
  6. washThe combined organic phases were washed with saturated NaHCO3 (2×130 ml), water (130 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. distillationDistillation (52° C.-55° C./0.06 torr)

Quellen und Nachweise

ORD-Eintrag
ord-9e8a519d4fb9463ca98233747331e2a5
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410000B1

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