Lithium Hydroxide → 4-(2,4,6-Trimethylphenyl)benzoic acid

HRID 915633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915633
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>O1CCOCC1.O>[CH3:19][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 13143477Methyl 2',4',6'-trimethyl[1,1'-biphenyl]-4-carboxylate

Produkt 1

HCID 227304674-(2,4,6-Trimethylphenyl)benzoic acidAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Combine 1-iodo-2,4,6-trimethylbenzene (2.966 g, 12.05 mmol), 4-carboxyphenylboronic acid (1.0 g, 6.026 mmol), Pd(OAc)2 (0.0067 g, 0.005 mmol), tetrabutylammonium bromide (0.388 g, 1.2055 mmol), and potassium phosphate (2.557 g, 12.05 mmol). Purge the reaction vessel with argon and add anhydrous dimethylformamide (20 mL) to the reaction mixture. Heat the sealed reaction vessel to 120° C. with stirring until completion as determined by TLC. Cool reaction mixture to room temperature. Add methyl iodide (1.0 mL, 36.63 mmol) to reaction mixture with continued stirring until completion. Dilute the reaction with ethyl acetate and filter though a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over magnesium sulfate, filter and evaporate. Purification by flash column chromatography yields 2′,4′,6′-trimethylbiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in dioxane (45 mL) and water (5 mL) containing 5 eq of LiOH with stirring at 60° C. Upon completion, evaporate the solvent, acidify the reaction mixture with hydrochloric acid, and extract with ethyl acetate. Dry the organics over magnesium sulfate, filter, and evaporate to yield 0.023 g (16%) of the title compound. MS (m/e): 239.1 (M−).

Aufarbeitung

  1. customUpon completion, evaporate the solvent
  2. extractionextract with ethyl acetate
  3. dry with materialDry the organics over magnesium sulfate
  4. filtrationfilter
  5. customevaporate

Quellen und Nachweise

ORD-Eintrag
ord-4af9d6cbeb604163b0db963872f15246
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

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