2-Oxobutanoic Acid → 2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

HRID 30493

Reaktionsgleichung

Reaktionsgleichung von HRID 30493
[O:1]=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[C:8]1([C:14]([CH3:24])([CH3:23])[CH:15]2[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH:16]2O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:21][C@H:18]1[CH2:17][C@@H:16]([O:4][C:3](=[O:5])[C:2](=[O:1])[CH2:6][CH3:7])[C@H:15]([C:14]([CH3:24])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:23])[CH2:20][CH2:19]1

Komponenten

5

Edukt 2

HCID 582-Oxobutanoic AcidHCID 577105(+)-8-Phenylmenthol

Produkt 1

HCID 110883962-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl esterAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 2.28 g 2-oxobutyric acid (2, 22.11 mmol, 1.3 eq), 4.04 g (−)-8-phenylmenthol (18, 17.02 mmol, 1.0 eq) and 169.9 mg para-toluenesulfonic acid monohydrate (0.884 mmol, 0.52 eq) in 48 mL benzene was heated to reflux for 20 h 35 min. After cooling down to room temperature, the solution was washed twice with 50 mL saturated aqueous sodium hydrogencarbonate solution, and subsequently with 50 mL water and 50 mL brine. The organic phase was dried over 5 g sodium sulfate and was filtered. The filter cake was washed with 10 mL benzene. The organic phase was evaporated to dryness in a rotary evaporator (40° C., 20 mbar) yielding the title compound (4.98 g, 92% by weight) as colorless solid.

Aufarbeitung

  1. temperatureto reflux for 20 h 35 min
  2. washthe solution was washed twice with 50 mL saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic phase was dried over 5 g sodium sulfate
  4. filtrationwas filtered
  5. washThe filter cake was washed with 10 mL benzene
  6. customThe organic phase was evaporated to dryness in a rotary evaporator (40° C., 20 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-e0866e356d694e0da29bc5cae5ef3ed2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423152B2

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