Sodium Hydroxide → 3-Cyclopentyl-2-phenylpropanoic acid

HRID 889599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889599
C[O:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([OH:17])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 462211553-Cyclopentyl-2-phenylpropionic acid methyl ester

Produkt 1

HCID 186266423-Cyclopentyl-2-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To title A compound, 3-cyclopentyl-2-phenylpropionic methyl ester (13.0 g, 56 mmol) in 100 mL of methanol is added a solution of 5.6 g (140 mmol) of NaOH in 8 mL of water. The reaction mixture is stirred at ambient temperature overnight. The methanol is evaporated and the residue is dissolved in 200 mL of water and extracted with ethyl ether. The aqueous phase is separated and adjusted to pH 2-3 with 1 N HCl and extracted with MTBE twice. The combined extracts are washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. The material is evaporated to a yellow oil that crystallizes to provide 3-cyclopentyl-2-phenylpropionic acid as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 1.7 (m, 2H), 2.1 (m, 2H), 2.2 (m, 3H), 2.4(m, 3H), 2.4 (m, 1H), 4.2 (t, J=7.7 Hz, 1H), 7.9 (m, 5H); LC/MS 236 (M+NH4+).

Aufarbeitung

  1. customThe methanol is evaporated
  2. dissolutionthe residue is dissolved in 200 mL of water
  3. extractionextracted with ethyl ether
  4. customThe aqueous phase is separated
  5. extractionextracted with MTBE twice
  6. washThe combined extracts are washed with saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe material is evaporated to a yellow oil
  9. customthat crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-3bc574c6b9864c999325dc5e769e919f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252931B2

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