Ammonium formate → 4-Methoxy-2-(propan-2-yl)phenol

HRID 38363

Reaktionsgleichung

Reaktionsgleichung von HRID 38363
O[C:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3].C([O-])=O.[NH4+]>CC(O)=O.O.[Pd]>[CH:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3]

Komponenten

6

Edukt 2

HCID 2723923Ammonium formateHCID 252417532-(2-Hydroxypropan-2-YL)-4-methoxyphenol

Produkt 1

HCID 183649974-Methoxy-2-(propan-2-yl)phenolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (50.57 g, 278 mmol) in 550 ml AcOH was added 10% Pd/C (as a slurry in 20 ml H2O). Ammonium formate (87.52 g, 1388 mmol) was added in portions. The mixture was warmed to 100° C. for 1 hour, cooled and filtered through a pad of celite. The celite pad was washed with ethyl acetate. The mother liquor was mixed with H2O and extracted with ethyl acetate. The combined organics were washed with H2O, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 2-isopropyl-4-methoxy-phenol (44.74 g, 97%) as a pale yellow oil.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered through a pad of celite
  3. washThe celite pad was washed with ethyl acetate
  4. additionThe mother liquor was mixed with H2O
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with H2O
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3eedd24e572d4ffd938deda1333a9efc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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