Reacción #1848932

Ecuación de reacción

water

(2Z,6E)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol

p-toluenesulfonic acid

→

tetrahydro-2-[[(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2H-pyran

Disolventes

3,4-dihydro-2H-pyran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónis extracted with ether
2. 2
   LavadoThe organic phase is washed with sodium bicarbonate solution
3. 3
   OtroAfter drying
4. 4
   Otroremoving the solvent the residue
5. 5
   Otrois chromatographed on silica gel with ether-hexane 1:1

Procedimiento

A solution of 1 g (0.0045 mol) (2Z,6E)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol in 32 ml of 3,4-dihydro-2H-pyran is treated at 0° with 91 mg of p-toluenesulfonic acid. The solution is stirred at the same temperature for 2 hours under argon. After the addition of 100 ml of water the mixture is extracted with ether. The organic phase is washed with sodium bicarbonate solution. After drying and removing the solvent the residue is chromatographed on silica gel with ether-hexane 1:1. There is obtained tetrahydro-2-[[(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2H-pyran which has the following bands in the IR spectrum: 1666 cm-1, 1444 cm-1, 1379 cm-1, 1116 cm-1, 1075 cm-1, 1020 cm-1.

Fuente