Water → Hexyl 2,2-bis(hexyloxy)propanoate

HRID 1518169

Reaktionsgleichung

Reaktionsgleichung von HRID 1518169
S([O-])([O:4][CH2:5][C:6]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:7])(=O)=O.[Na+].[OH2:24]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:8][C:6]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:7])[C:5]([O:24][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:4])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 2

HCID 962WaterHCID 46945113Sodium 2,2-bis(hexyloxy)propyl sulfate2×

Produkt 1

HCID 46945489Hexyl 2,2-bis(hexyloxy)propanoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of methyl pyruvate 1 (10.0 g, 98.0 mmol) in toluene (100 mL) is added 1-hexanol 2 (40.1 g, 392 mmol) and p-TsOH (186 mg, 0.98 mmol). The mixture is heated to reflux for 10 hours with azeotropic removal of water from the reaction mixture. The reaction is quenched with saturated NaHCO3 (100 mL), and the reaction mixture is extracted with ethyl acetate (2×100 mL). The combined organic layers are washed with brine (100 mL) and dried over anhydrous sodium sulfate. The solvent is removed and the residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane) to give hexyl 2,2-bis(hexyloxy)propanoate 3 (29.5 g, 84%) as a colorless oil: Rf (15% EtOAc/hexane)=0.53; IR (thin film, cm−1) 2956, 2930, 2860, 1746 (C═O), 1467, 1280, 1137, 1062. 1H NMR (600 MHz, CDCl3) δ 4.14 (t, J=7.2 Hz, 2H), 3.48 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 3.35 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 1.65-1.63 (m, 2H), 1.59-1.54 (m, 4H), 1.49 (s, 3H), 1.35-1.24 (m, 18H), 0.86 (t, J=7.2 Hz, 9H); 13C NMR (150 MHz, CDCl3) δ 170.2, 99.5, 65.4, 62.6, 31.7, 31.3, 29.7, 28.5, 25.8, 25.5, 22.6, 22.5, 21.9, 14.0, 13.9.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. customThe reaction is quenched with saturated NaHCO3 (100 mL)
  3. extractionthe reaction mixture is extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers are washed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed
  7. customthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3596ec54c4954532919c961a9e39e168
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232423B2

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