Reaktion #1120415

Reaktionsgleichung

methyl 2-(4-phenylphenoxy)-2-methylpropionate

sodium hydride

(trans) 3,3,5-trimethylcyclohexanol

→

crystals

(TRANS) 3,3,5-TRIMETHYLCYCLOHEXYL 2-(4-PHENYLPHENOXY)-2-METHYLPROPIONATE

Lösungsmittel

heptane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeappropriately equipped
2. 2
   Sonstigefor progressively separating the binary heptane/methanol mixture, which boils at 59° C.
3. 3
   Temperaturthe mixture is cooled
4. 4
   Waschenwashed carefully with an alkaline aqueous solution
5. 5
   workup.ADDITIONAfter chromatography on a silica column with a mixture of ethyl acetate and petroleum ether and recrystallization from 90% isopropanol

Vorschrift

27 g of methyl 2-(4-phenylphenoxy)-2-methylpropionate (0.1 mol) and 0. 3 g of sodium hydride as a 60% dispersion in oil are added to 14.2 g of (trans) 3,3,5-trimethylcyclohexanol (0.1 mol) dissolved in 500 ml of heptane. The stirred mixture is brought to the boil in a distillation apparatus appropriately equipped for progressively separating the binary heptane/methanol mixture, which boils at 59° C.; the operation requires 4 to 5 hours; the mixture is cooled and then washed carefully with an alkaline aqueous solution, then an acidic aqueous solution and finally pure water. After chromatography on a silica column with a mixture of ethyl acetate and petroleum ether and recrystallization from 90% isopropanol, the title derivative is obtained in the form of silky crystals melting at 96° C. TLC performed under the previous conditions gives a single spot of Rf 0. 90. The IR spectrum has characteristic bands at 2950-2850, 1745 and 1640 cm-1.

Quelle