Reaction #2328975

Reaction equation

trans-4-vinyl cyclohexane carboxylic acid

trimethylsilyl chloride

→

methyl trans-4-vinylcyclohexanecarboxylate

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureby refluxing for 6 hours
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   workup.ADDITION150 mL of hexane was added
4. 4
   Otherthe methanol layer was separated
5. 5
   Extractionthe methanol layer was extracted with hexane
6. 6
   Washthe mixture was washed with saturated saline
7. 7
   DryingThe organic layer was dried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated

Procedure

All of trans-4-vinyl cyclohexane carboxylic acid was dissolved in 120 mL of methanol and 0.1 g of trimethylsilyl chloride was added, followed by refluxing for 6 hours. The solution was cooling to room temperature and then concentrated under reduced pressure. 150 mL of hexane was added and the methanol layer was separated, and then the methanol layer was extracted with hexane. After combining with the organic layer, the mixture was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 29.5 g of methyl trans-4-vinylcyclohexanecarboxylate.

Source