Water → {2',3',5',6'-Tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

HRID 453423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453423
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([OH:17])=[C:11]([CH3:18])[C:10]=2[CH3:19])[CH:6]=[CH:7][CH:8]=1.CC1C=CC(S(O[CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:19][C:10]1[C:11]([CH3:18])=[C:12]([O:17][CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonateHCID 593426133'-(Hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-ol

Produkt 1

HCID 59342583{2',3',5',6'-Tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3′-(hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-ol (0.616 g, 2.40 mmol) and 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (1.05 g, 3.60 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.597 g, 4.32 mmol), and the mixture was stirred at 90° C. for 12 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (0.577 g, yield 85%) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20)
  6. customthe obtained crystals were recrystallized from heptane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f0176eb1b777450cb3202b7769783434
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492430B2

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