Acetic Acid → (1,1'-Biphenyl)-2,3'-diol

HRID 324602

Reaktionsgleichung

Reaktionsgleichung von HRID 324602
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C[CH2:10][C:11](=[O:14])[CH2:12][CH3:13].OS(O)(=O)=O.[C:20](O)(=O)C>>[CH:3]1[CH:2]=[C:1]([C:8]2[CH:20]=[CH:13][CH:12]=[C:11]([OH:14])[CH:10]=2)[C:6]([OH:7])=[CH:5][CH:4]=1

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 335O-CresolHCID 1118Sulfuric AcidHCID 7288Ethyl ketone

Produkt 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Versuchsvorschrift

To a solution of o-cresol (5 g, 46.3 mmol) and 3-pentanone (2 g, 23.2 mmol) in acetic acid (20 mL) was added conc H2SO4 (4 mL). The reaction mixture was stirred at ambient temperature for 3 days, poured over ice, and diluted with 1:5 ethyl acetate/hexanes. The organic fraction was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 5% ethyl acetate in hexanes) afforded 2.2 g of diphenol 6. 1HNMR (CDCl3) δ: 6.90 (d, J=2 Hz, 2 H, Ar—H), 6.95 (dd, J=2 Hz, J=8.6 Hz, 2 H, Ar—H), 6.64 (d, J=8.6 Hz, 2 H, Ar—H), 2.21 (s, 6 H, Ar—CH3), 2.0 (q, J=7.3 Hz, 4 H, CH2CH3), 0.60 (t, J=7.3 Hz, 4 H, CH2CH3).

Aufarbeitung

  1. additionpoured over ice
  2. customThe organic fraction was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-01999415c2004771aa7852c72a5058de
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218430B1

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