Reaction #1605782

Reaction equation

pyridine

pyridine

triphosgene

diethylamine

2,3,6-trimethylcyclohexanol

→

desired product

Yield 51.8%

Diethyl-carbamic acid 2,3,6-trimethyl-cyclohexyl ester

Yield 51.8%

Solvents

dichlormethane

dichlormethane

dichlormethane

Conditions

Workup

1. 1
   Otherto come to ambient temperature
2. 2
   Otherquenched with water
3. 3
   OtherAfter separation of the phases
4. 4
   Extractionthe water phase was extracted once with dichlormethane
5. 5
   Concentrationthe combined organic phases were concentrated
6. 6
   workup.DISTILLATIONThe raw product was purified by distillation and column chromatography

Procedure

4.27 g (30 mmol) of 2,3,6-trimethylcyclohexanol were placed with 110 ml dichlormethane in a 250 ml vessel at room temperature and 3.08 g (39 mmol) of pyridine were added. The reaction mixture was cooled to 0° C. and 3.56 g (12 mmol) of triphosgene in 15 ml dichlormethane were added dropwise. After five minutes 2.37 g (30 mmol) pyridine were added. Subsequently, 2.19 g (30 mmol) of diethylamine in 15 ml dichlormethane were added dropwise, the resulting mixture was allowed to come to ambient temperature and then quenched with water. After separation of the phases, the water phase was extracted once with dichlormethane and the combined organic phases were concentrated. The raw product was purified by distillation and column chromatography to yield 1.5 g of the desired product as a mixture of isomers with a purity of 99.4%.

Source