Sodium Hydroxide → 6-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid

HRID 48316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48316
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:23]([O:25]CC)=[O:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])C.[OH-].[Na+]>C(O)C.O>[C:4]([C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:34])[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:16])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]([OH:25])=[O:24])([OH:35])=[O:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 116418176-(5-Ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester

Produkt 1

HCID 102971706-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acidAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 6-(5-ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester (6.00 g, 12.0 mmol) and sodium hydroxide (3.1 g, 74.0 mmol) in ethanol (40 mL) and deionized water (4 mL) was heated to reflux for 2 h. The ethanol was evaporated in vacuo and the residue was dissolved in water (20 mL) and extracted with diethyl ether (20 mL). The organic phase was discarded. The aqueous layer was acidified with 2 N hydrochloric acid (15 ml) to pH 2-3 and extracted with diethyl ether (4′ 50 mL). The combined organic layers were washed with brine (15 mL), dried over MgSO4, and concentrated in vacuo. The residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1) to give 6-(5-carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid (3.63 g, 68%) as a yellowish oil. 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 7.42-7.20 (m, 10H), 2.45 (t, J=7.3 Hz, 4H), 2.15-1.80 (m, 4H), 1.65-1.45 (m, 4H), 1.56 (s, 6H), 1.40-1.15 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): d (ppm): 182.43, 142.89, 128.41, 126.91, 126.05, 50.00, 38.53, 31.80, 30.00, 24.03, 22.40. HRMS (LSIMS, nba): Calcd. for C26H35O4S1 (MH+): 443.2256, found: 443.2231.

Aufarbeitung

  1. temperatureto reflux for 2 h
  2. customThe ethanol was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. extractionextracted with diethyl ether (20 mL)
  5. extractionextracted with diethyl ether (4′ 50 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-78e05ab6bfa14117b27204f62c1b9645
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703422B2

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