Catechol → 2-Isobutoxyphenol

HRID 1917017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917017
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:16][CH:17]([CH3:19])[CH3:18]>CC#N>[CH2:16]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH:17]([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 289CatecholHCID 10556Isobutyl iodideHCID 10796Cesium carbonate

Produkt 1

HCID 6911612-IsobutoxyphenolAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A 50 mL round-bottom flask was charged with catechol (499 mg, 4.53 mmol), CH3CN (4.5 mL), and Cs2CO3 (1.50 g, 4.60 mmol) and purged with nitrogen. This white suspension was allowed to stir for 10 minutes prior to the addition of 1-iodo-2-methylpropane (1.67 g, 9.06 mmol). The reaction was brought to reflux and allowed to stir for 18 h. After cooling to room temperature the solvent was concentrated in vacuo, and the residue partitioned between ethyl acetate (50 mL) and 1 N HCl (50 mL). The organic layer was separated, dried, filtered, and concentrated in vacuo. Flash chromatography (3:1 hexane:ethyl acetate) afforded a yellow oil weighing 316 mg (30% yield). 1H NMR (CDCl3): δ 1.05 (dd, J=1.95 Hz, J=6.85 Hz, 6H), 2.13 (s-7, J=6.60 Hz), 3.81 (d, J=6.60 Hz), 6.81-6.88 (m, 3H), 6.93-6.95 (m, 1H); 13C NMR (CDCl3): δ 19.39, 28.38, 75.31, 111.77, 114.57, 120.22, 121.12, 121.44, 146.16.

Aufarbeitung

  1. custompurged with nitrogen
  2. temperatureto reflux
  3. stirringto stir for 18 h
  4. concentrationwas concentrated in vacuo
  5. customthe residue partitioned between ethyl acetate (50 mL) and 1 N HCl (50 mL)
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customFlash chromatography (3:1 hexane:ethyl acetate) afforded a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-d970d7715482482a942eedeb6ad3bd36
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618162B2

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