Water → 10-(Propylthio)decanoic acid

HRID 362760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362760
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[OH-].[K+].O.[CH2:17]([SH:20])[CH2:18][CH3:19]>CO>[CH2:17]([S:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:18][CH3:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 14271210-Bromodecanoic Acid

Produkt 1

HCID 1817610010-(Propylthio)decanoic acidAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
69 °C

Versuchsvorschrift

10-bromodecanoic acid (1.0 g, 3.98 mmol) was added to a solution of potassium hydroxide (0.893 g, 15.9 mmol) in 1-propanethiol (30 mL) and methanol (30 mL) and stirred at 69° C. for 18 hrs. The reaction was allowed to cool to room temperature after the addition of 20 mL water. After acidification to pH=1 and extraction into ethyl acetate, the organic phase was dried over sodium sulfate and solvent removed at reduced pressure to yield a white crystalline powder. The product was purified by silica column chromatography in 8% ethyl acetate/hexane/0.3% formic acid and recrystallization from hexane to yield 10-(propylthio)decanoic acid (210 mg, 21%), mp 42°-43.5° C.; 1H NMR (300 MHz, CDCl3) δ0.96 (t, 3H, J=7.3, CH3) 1.15-1.40 (bm, 10H, methylene envelope), 1.49-1.64 (bm, 6H, CH3CH2CH2SCH2CH2, CH2CH2COOH), 2.32 (t, 2H, J=7.6, CH2COOH), 2.40-2.55 (bm, 4H, CH3CH2CH2SCH2), 10.93 (Br, 1H, COOH); 13C NMR (75.4 MHz, CDCL3) δ 13.64, 23.09, 24.71, 28.96, 29.07, 29.13, 29.24, 29.36, 29.77, 32.16, 34.10, 34.28, 179.98; m/z 247 (M+H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionAfter acidification to pH=1 and extraction into ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate and solvent
  4. customremoved at reduced pressure
  5. customto yield a white crystalline powder
  6. customThe product was purified by silica column chromatography in 8% ethyl acetate/hexane/0.3% formic acid
  7. customrecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-132657c483e34af9bcb941ddb098653f
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05871954

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