Reacción #366674

Ecuación de reacción

KBr

(R)-(+)-limonene oxide

imidazole

hydrochloric acid

→

(+)-(1S,2S,4R)-2-(1-Imidazolyl)-1-methyl-4-(1-methylethenyl)cyclohexanol

Disolventes

CHCl3

water

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA reflux condenser was attached
2. 2
   Otrothe flask was set in an oil bath
3. 3
   Temperaturathe reaction mixture was cooled to 25° C.
4. 4
   Extracciónextracted with diethyl ether (7×30 mL)
5. 5
   TemperaturaThe aqueous layer was cooled to 0° C.
6. 6
   workup.ADDITIONtreated with solid sodium hydroxide until the solution
7. 7
   ExtracciónThe solution was extracted with methylene chloride (10×30 mL)
8. 8
   Otrothe combined extracts were dried
9. 9
   OtroThe solvent was removed in vacuo
10. 10
    Otroleaving a semi-solid material that
11. 11
    TemperaturaThe solution was cooled
12. 12
    Otroto give a white, crystalline solid, mp 126-128° C.

Procedimiento

To (R)-(+)-limonene oxide (6.88 mmol, 1.047 g, 1.13 mL) were added 6 mL of deionized water and imidazole (21 mmol, 1.43 g) at 25° C. A reflux condenser was attached and the flask was set in an oil bath that was heated to 100° C. After 5.0 h at 100° C., the reaction mixture was cooled to 25° C., acidified with 12M hydrochloric acid, and extracted with diethyl ether (7×30 mL). The aqueous layer was cooled to 0° C. and treated with solid sodium hydroxide until the solution was strongly basic to litmus (pH 10). The solution was extracted with methylene chloride (10×30 mL) and the combined extracts were dried. The solvent was removed in vacuo leaving a semi-solid material that was taken up in hot diethyl ether. The solution was cooled to give a white, crystalline solid, mp 126-128° C.; [α]25D=+11.4 (c=3.5 in CHCl3); IR (KBr) 3210.0, 2850.0 cm−1.

Fuente