Methanol → 1,1-Diphenyl-10-undecen-1-ol

HRID 275472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275472
[C:1]([O:13]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>C1COCC1>[C:16]1([C:1]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 12729Ethyl 10-undecenoateHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 200883261,1-Diphenyl-10-undecen-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 10.6 g of ethyl undecylenate in 100 mL of THF at 0° C. was added, over 1 hr, 40 mL of 3M phenyl magnesium bromide. The mixture was warmed to room temperature and stirred for 75 hrs. Methanol, 10 mL, was added to quench the excess Grinard reagent and the solvent was distilled in vacuo. The residue was shaken with diethyl ether and dilute hydrochloric acid. The ether layer was washed with water and saturated sodium hydrogen carbonate, dried, and concentrated in vacuo to give 18.3 g of crude product, which was then chromatographed on silica gel with chloroform as the eluent, to give 13.7 g of 1,1-diphenyl-10-undecen-1-ol which is characterized by:

Aufarbeitung

  1. customto quench the excess Grinard reagent
  2. distillationthe solvent was distilled in vacuo
  3. stirringThe residue was shaken with diethyl ether and dilute hydrochloric acid
  4. washThe ether layer was washed with water and saturated sodium hydrogen carbonate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give 18.3 g of crude product, which
  8. customwas then chromatographed on silica gel with chloroform as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-929948ed7ac140a39bab7591f6d74b97
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393797

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