Reaction #1747

Reaction equation

sodium hydroxide

trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol

triethylamine

4-chlorobenzoylchloride

→

trans-O-(4-Chlorobenzoyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol

Solvents

water

methylene chloride

Conditions

Workup

1. 1
   Temperaturerefluxed for 3 hours
2. 2
   TemperatureAfter cooling
3. 3
   Otherthe methylene chloride phase is separated off
4. 4
   Extractionthe aqueous phase is extracted once more with methylene chloride
5. 5
   DryingThe combined organic phases are dried over sodium sulphate
6. 6
   Otherevaporated down in vacuo
7. 7
   OtherThe solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1)
8. 8
   OtherWhite crystals are obtained with a melting point of 94°-95° C.

Procedure

A solution of 1.0 g (0.0043 mol) of trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 0.6 ml of triethylamine in 50 ml of methylene chloride is combined, dropwise, with 0.75 g (0.0043 mol) of 4-chlorobenzoylchloride, with stirring, and refluxed for 3 hours. After cooling, 50 ml of water are added, the mixture is adjusted to pH 12-13 with sodium hydroxide solution, the methylene chloride phase is separated off and the aqueous phase is extracted once more with methylene chloride. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1). White crystals are obtained with a melting point of 94°-95° C.

Source