Water → (5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 226548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226548
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)C.O.O[Li].O>C1COCC1>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:30])=[O:3])[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=2)[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24771790Ethyl [5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]acetate

Produkt 1

HCID 11501912(5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (120 g, 0.29 mol) in THF (1.2 L) was added water (240 mL), LiOH.H2O (16 g, 0.32 mol) and the resulting mixture was stirred at room temperature for 16 h. The solution was filtered and concentrated in vacuo to remove THF. The resulting thick liquid was acidified to pH 2 by adding 2N aqueous HCl solution and the white suspension was mechanically stirred for 1 h at room temperature. The wet white product was recovered after filtration and dissolved in EtOAc (500 mL). The organic layer was separated from water, dried (MgSO4) and concentrated in vacuo to obtain (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid (105 g, 94%).

Aufarbeitung

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. customto remove THF
  4. additionby adding 2N aqueous HCl solution
  5. stirringthe white suspension was mechanically stirred for 1 h at room temperature
  6. customThe wet white product was recovered
  7. filtrationafter filtration
  8. dissolutiondissolved in EtOAc (500 mL)
  9. customThe organic layer was separated from water
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3dd23bca1b5b4f94a80a5f5a960991bc
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557244B2

Notizen zur Reaktion

Wird geladen…