Benzyl Alcohol → (1-Benzyloxycarbonylmethyl-cyclohexyl)-acetic acid

HRID 455899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455899
[C:1]12([CH2:12][C:11](=[O:13])[O:10][C:8](=[O:9])[CH2:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.N1C=CC=CC=1.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C)C=CC=CC=1>>[CH2:20]([O:27][C:11]([CH2:12][C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 1140TolueneHCID 27342891,1-Cyclohexanediacetic Anhydride

Produkt 1

HCID 14036669(1-Benzyloxycarbonylmethyl-cyclohexyl)-acetic acidAusbeute 90,1 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1,1-cyclohexanediacetic anhydride (5.0 g, 27 mmol), pyridine (2.2 mL, 27 mmol), and benzyl alcohol (2.8 mL, 27 mmol) and toluene (5.0 mL, 47 mmol) was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 1 N HCl. The organic layer was washed three times with 1 N HCl and brine. The organic extract was dried over sodium sulfate, filtered, and concentrated to dryness to yield the title compound (7.06 g, 89% yield) as a clear oil. 1H NMR (DMSO-d6, 400 mHz) δ (ppm): 11.96 (s, 1H), 7.32 (m, 5H), 5.03 (s, 2H), 2.52 (s, 2H), 2.34 (s, 2H), 1.40 (m, 10H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and 1 N HCl
  3. washThe organic layer was washed three times with 1 N HCl and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8287b0aa26ad4d9bbe918e5f7b621dd1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497287B2

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