Phenol → 2-Isobutylphenol

HRID 2184642

Reaktionsgleichung

Reaktionsgleichung von HRID 2184642
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:8][C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>CCOCC>[OH:8][C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[CH2:10]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH:9]([CH3:19])[CH3:18]

Komponenten

8

Edukt 5

HCID 996PhenolHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 516892Sodium Bicarbonate

Produkt 2

HCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 931442-IsobutylphenolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-Hydroxy-isobutyrophenone was prepared from phenol following the procedure described in Canadian Journal of Chemistry, 31, 1956, 851. To a solution of 2-hydroxy-isobutyrophenone (2g, 12.2 mmol) in trifluroacetic acid (14 g, 122 mmol) was slowly added triethylsilane (26.8 mmol). The solution was stirred at room temperature for 6 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by ether. The layers were separated, and the aqueous layer was extracted with ether. The organic layers were combined, dried over magnesium sulfate, and concentrated. The crude material was distilled under vacuum (about 9.3×10−4 MPa, 75° C.). The distillate was washed with potassium hydroxide solution, followed by addition of hydrogen chloride solution, and extraction with ether. The ether layers were combined, dried over magnesium sulfate, and concentrated to give 1.0 g (55%) of 2-isobutylphenol. 1H NMR (300 Mhz, δ, CDCl3): 7.0 (m, 2H), 6.8 (t, 1H), 6.7 (d, 1H), 4.6 (br. s, 1H), 2.4 (d, 2H), 1.9 (s, 1H), 0.9 (d, 6H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe crude material was distilled under vacuum (about 9.3×10−4 MPa, 75° C.)
  6. washThe distillate was washed with potassium hydroxide solution
  7. additionfollowed by addition of hydrogen chloride solution, and extraction with ether
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a68301cfd4842b68bb8abdd0dc9c3f1
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399534B2

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