Lithium Hydroxide → 2-Chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acid

HRID 1879104

Reaktionsgleichung

Reaktionsgleichung von HRID 1879104
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[CH:15][C:3]=1[C:4]([O:6]CC1C=CC=C(Cl)C=1)=[O:5].[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[CH:15][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 59760043(3-Chlorophenyl)methyl 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoate

Produkt 1

HCID 597600492-Chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acidAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of (3-chlorophenyl)methyl 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoate (970 mg, 2.3 mmol) in dioxane (30 ml) and water (15 ml) was treated with lithium hydroxide (monohydrate) (145 mg, 3.5 mmol, 1.5 eq). The resulting mixture was stirred at room temperature for 2 hours. The solvent was then evaporated in vacuo, the residue take up into water (50 ml) and washed with ether (100 ml). The aqueous layer was then acidified with 2M HCl the extracted with ether (2×150 ml). Organic layers combined, washed with brine, dried and evaporated in vacuo to afford the title product as a white solid (600 mg). MS (ES−) m/z 295 [M−H]− (C14H1035Cl2O3). 1H-NMR (400 MHz, d6-DMSO) δ 5.17 (2H, s), 7.17-7.20 (1H, m), 7.38-7.53 (6H, m), 13.4 (1H, s).

Aufarbeitung

  1. customThe solvent was then evaporated in vacuo
  2. washwashed with ether (100 ml)
  3. extractionextracted with ether (2×150 ml)
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c62acdd9fd5c45ae8bab147d1613d69c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314147B2

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