Lithium hydroxide, monohydrate → 3-(4-Chlorophenyl)-2-phenylpropanoic acid

HRID 1446376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446376
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 16098314Methyl 3-(4-chlorophenyl)-2-phenylpropionate

Produkt 1

HCID 222705593-(4-Chlorophenyl)-2-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of methyl 3-(4-chlorophenyl)-2-phenylpropionate (Step A, 20 g, 74 mmol) in acetonitrile (100 mL) and water (100 mL) was added lithium hydroxide monohydrate (8.8 g, 0.21 mol). After stirring at room temperature for 3 days, the volatile materials were removed by concentrating on a rotary evaporator and the residue was partitioned between water (300 mL) and hexane/ether (1:1, 200 mL). The water layer was separated, acidified to pH=2-3, and extracted with ethyl acetate (2×200 mL) The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.34-7.10 (m, 9H), 3.82 (dd, 1H), 3.36 (dd, 1H), 2.98 (dd, 1H).

Aufarbeitung

  1. customthe volatile materials were removed
  2. concentrationby concentrating on a rotary evaporator
  3. customthe residue was partitioned between water (300 mL) and hexane/ether (1:1, 200 mL)
  4. customThe water layer was separated
  5. extractionextracted with ethyl acetate (2×200 mL) The combined organic extracts
  6. dry with materialwere dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c2832be6ba1540ccbd33de9b9b0fcb76
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667053B2

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