Reaktion #58771

Reaktionsgleichung

2-oxobutyric acid

(−)-8-phenylmenthol

→

title compound

Ausbeute 92.5%

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

Ausbeute 92.5%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 20 h 35 min
2. 2
   Waschenthe solution was washed twice with 50 mL saturated aqueous sodium hydrogencarbonate solution
3. 3
   TrocknenThe organic phase was dried over 5 g sodium sulfate
4. 4
   Filtrationwas filtered
5. 5
   WaschenThe filter cake was washed with 10 mL benzene
6. 6
   SonstigeThe organic phase was evaporated to dryness in a rotary evaporator (40° C., 20 mbar)

Vorschrift

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.

Quelle