Réaction #2328974

Équation de réaction

water

potassium t-butoxide

methoxymethyltriphenylphosphonium bromide

methyl 4-formylcyclohexanecarboxylate

→

methyl 4-vinylcyclohexanecarboxylate

Solvants

tetrahydrofuran

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONthe resulting solution was added dropwise at −6 to 4° C. over 50 minutes
2. 2
   workup.STIRRINGAfter stirring at 0 to 4° C. for 30 minutes
3. 3
   workup.DISTILLATIONThe solvent of the reaction mixture was distilled off under reduced pressure and 500 mL of hexane
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGby stirring at room temperature for 30 minutes
6. 6
   FiltrationThe precipitate was filtered
7. 7
   Lavagewashed again with 500 mL of hexane
8. 8
   Lavagethe mixture was washed in turn with a mixed solution of methanol and water (1:1), water, and saturated saline
9. 9
   SéchageAfter drying over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
11. 11
    Autreto obtain 81.2 g of an oily substance
12. 12
    workup.DISTILLATIONThe oily substance was distilled under reduced pressure
13. 13
    Autreto obtain 57.3 g of methyl 4-vinylclohexanecarboxylate
14. 14
    workup.ADDITIONa mixture of a cis isomer

Mode opératoire

297.4 g of methoxymethyltriphenylphosphonium bromide was dispersed in 900 mL of tetrahydrofuran (THF) and 95.6 g potassium t-butoxide was added at −8° C. in 3 minutes. After stirring for 30 minutes, all of methyl 4-formylcyclohexanecarboxylate was dissolved in 270 mL of THF and the resulting solution was added dropwise at −6 to 4° C. over 50 minutes. After stirring at 0 to 4° C. for 30 minutes, 15 mL of water was added. The solvent of the reaction mixture was distilled off under reduced pressure and 500 mL of hexane was added, followed by stirring at room temperature for 30 minutes. The precipitate was filtered and the precipitate was suspended and washed again with 500 mL of hexane. After combining with the hexane filtrate, the mixture was washed in turn with a mixed solution of methanol and water (1:1), water, and saturated saline. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 81.2 g of an oily substance. The oily substance was distilled under reduced pressure to obtain 57.3 g of methyl 4-vinylclohexanecarboxylate. A boiling point was 122 to 127° C./48 hPa. The gas chromatography analysis revealed that, the resulting substance is a mixture of a cis isomer and a trans isomer in a mixing ratio of 26:74.

Source