Water → HCID 59760044, Verbindung

HRID 1879126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879126
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([CH:26]=2)[C:15]([O:17]CC2C=CC=C(Cl)C=2)=[O:16])[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([CH:26]=2)[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 59760048HCID 59760048, Verbindung

Produkt 1

HCID 59760044HCID 59760044, VerbindungAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of (3-chlorophenyl)methyl 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoate from the preparation of Intermediate 84 described above (2.67 g, 6.66 mmol) in 1,4-dioxane (20 ml) and water (10 ml) was treated with lithium hydroxide (419 mg, 9.99 mmol, 1.5 eq). The resulting mixture was stirred at room temperature under argon overnight. A further portion of lithium hydroxide (419 mg, 9.99 mmol, 1.5 eq) was added and stirring continued at room temperature for 2 hours. Stirring continued at room temperature overnight. The solvent was then evaporated to dryness and then partitioned between 2M HCl (100 ml) and diethylether (100 ml). The organic layer was separated and passed through a hydrophobic frit to remove any water and evaporated to dryness to afford the title compound as a white solid (1.98 g) (contains 12% impurity). No further purification carried out. MS (ES−) m/z 275 [M−H]− (C15H1335ClO3).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature for 2 hours
  3. stirringStirring
  4. waitcontinued at room temperature overnight
  5. customThe solvent was then evaporated to dryness
  6. custompartitioned between 2M HCl (100 ml) and diethylether (100 ml)
  7. customThe organic layer was separated
  8. customto remove any water
  9. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f5b1f8430412479eb4de1853217170be
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314147B2

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