Acetone → 6-Hydroxy-2,2-dimethylchroman-4-one

HRID 567053

Reaktionsgleichung

Reaktionsgleichung von HRID 567053
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].N1C[CH2:15][CH2:14][CH2:13]1.CC(C)=O>C(#N)C.CC(=O)OCC>[CH3:13][C:14]1([CH3:15])[CH2:1][C:2](=[O:3])[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=2)[O:11]1

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 102792-AcetylhydroquinoneHCID 31268Pyrrolidine

Produkt 1

HCID 35198596-Hydroxy-2,2-dimethylchroman-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A reaction mixture of 100 g (0.65 mol) of 2,5-dihydroxyacetophenone in 1 l of acetonitrile, 130 ml (1.55 mol) of pyrrolidine and 290 ml (3.95 mol) of acetone was heated to 45° C. for 8 h. The solvents were then stripped off in vac. and the residue was dissolved in 1 l of EA. The organic phase was washed twice with dilute hydrochloric acid, stirred with activated carbon and dried over magnesium sulfate and largely concentrated. After stirring the residue with petroleum ether and filtering off the precipitate with suction, 102 g of 2,2-dimethyl-6-hydroxychroman-4-one, m.p. 158° C., were obtained.

Aufarbeitung

  1. washThe organic phase was washed twice with dilute hydrochloric acid
  2. dry with materialdried over magnesium sulfate
  3. concentrationlargely concentrated
  4. stirringAfter stirring the residue with petroleum ether
  5. filtrationfiltering off the precipitate with suction, 102 g of 2,2-dimethyl-6-hydroxychroman-4-one, m.p. 158° C.
  6. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-656dc5f435c44ad0858c3ba105c8cba2
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06177449B1

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