2,6-Dimethylhydroquinone → 5,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

HRID 2102982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102982
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4].[CH:11]([C:13]1(O)[CH2:16][CH2:15][CH2:14]1)=[CH2:12]>O1CCOCC1.C(OCC)(=O)C>[CH3:10][C:5]1[C:3]([OH:4])=[C:2]([CH3:1])[CH:8]=[C:7]2[C:6]=1[CH2:12][CH2:11][C:13]1([O:9]2)[CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 2

HCID 695602,6-DimethylhydroquinoneHCID 122509441-Ethenylcyclobutan-1-ol

Produkt 1

HCID 115502985,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-olAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,6-dimethylhydroquinone (2.36 g) and BF3-ether (4.47 mL) in dioxane (10 mL) was added 1-vinyl-cyclobutanol (1.58 g) in dioxane (5 mL) over 50 min at 110° C. under nitrogen. The reaction was refluxed for one additional hour. The solution was diluted with ethyl acetate and washed with water and brine, dried and evaporated. The residue was chromatographed (silica gel, hexane-ethyl acetate 1% to 5%) gave 1.36 g of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol.

Aufarbeitung

  1. temperatureThe reaction was refluxed for one additional hour
  2. washwashed with water and brine
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed (silica gel, hexane-ethyl acetate 1% to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-8432fab18a064b89bf58f106b343089a
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

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