tert-Butanol → beta-Methylenephenethyl alcohol

HRID 17783

Reaktionsgleichung

Reaktionsgleichung von HRID 17783
CC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:11]([OH:15])(C)(C)C.[Se](=O)=O.C1(C(C)=C)C=CC=CC=1>C(Cl)Cl.C(O)(=O)C>[OH:15][CH2:11][C:9]([C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH2:10]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 7407Alpha-MethylstyreneHCID 15600DecaneHCID 24007Selenium Dioxide

Produkt 1

HCID 80106beta-Methylenephenethyl alcoholAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 12.5 ml of decane solution of 5 to 6 mol/L of per-tert-butylalcohol is diluted with 50 ml of methylene chloride, then 111 mg of selenium dioxide and 90.1 mg of an acetic acid were added thereto to react while stirring at room temperature for 30 min. Then, 6.5 ml of 2-phenylpropene was added to the reaction solution to react while stirring for 72 hours, followed by condensation under reduced pressure, and purification by silica gel column chromatography to obtain 3.98 g of 3-hydroxy-2-phenylpropene (yield: 59%). Measurement results by 1H-NMR and 13C-NMR of 3-hydroxy-2-phenylpropene obtained are shown below.

Aufarbeitung

  1. customto react
  2. customto react
  3. stirringwhile stirring for 72 hours
  4. customfollowed by condensation under reduced pressure, and purification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-19597bdefb3548119f1a52e9b0ae7935
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741242B2

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