3-Methyl-2-buten-1-OL → HCID 86605473, Verbindung

HRID 2102980

Reaktionsgleichung

Reaktionsgleichung von HRID 2102980
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4].[CH3:11][C:12]([CH3:16])=[CH:13][CH2:14]O>O1CCOCC1>[CH3:1][C:2]1[C:8]([CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11])=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4]

Komponenten

4

Edukt 2

HCID 111733-Methyl-2-buten-1-OLHCID 692112,5-Dimethylhydroquinone

Produkt 1

HCID 86605473HCID 86605473, VerbindungAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2,5-Dimethylbenzoquinone (5 g) in ethyl acetate was shaken with an aqueous solution of sodium hydrosulfite. The organic layer was separated, washed, dried and evaporated to yield 2,5-dimethylhydroquinone. To a solution of 2,5-dimethylhydroquinone (5 g), prepared as described above, and 3-methyl-2-buten-1-ol (3.1 g) in dioxane (20 mL) was added BF3-ether (4.5 mL) at room temperature under nitrogen. The solution was stirred at room temperature for one hour, extracted with ethyl acetate, washed with water and dried. The mixture containing starting material and alkylated product was hydrogenated in methanol (100 mL) with 5 drops of concentrated HCl in the presence of Pd/C (10%, 200 mg) at60 psi for 18 hours. Workup and chromatography (silica gel hexane-ethyl acetate 5% to 12%) gave 2 g of the desired product, 2,5-dimethyl-3-(3-methyl-butyl)-hydroquinone.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. additionThe mixture containing
  5. waitwas hydrogenated in methanol (100 mL) with 5 drops of concentrated HCl in the presence of Pd/C (10%, 200 mg) at60 psi for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-e0423c6e2b61468f832782cdc85003c5
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

Verknüpfte Notizen

Wird geladen…