반응 #1102871

반응 방정식

4,5-di(hydroxymethyl)-1-methylcyclohexene

sodium carbonate

propionic acid

4,5-di(hydroxymethyl)-1-methylcyclohexene oxide

vinyl acetate

vinyl acetate

m-chloroperbenzoic acid

4,5-di(hydroxymethyl)-1-methylcyclohexene oxide

→

4,5-di(vinyloxymethyl)-1-methylcyclohexene oxide

수율 80.0%

용매

toluene

반응 조건

후처리

1. 1
   온도Maintaining the temperature of the reaction mixture
2. 2
   workup.ADDITIONadded dropwise
3. 3
   기타fifteen minutes
4. 4
   기타at 95° C
5. 5
   workup.ADDITIONAfter the completion of dropwise addition
6. 6
   기타As the result of gas chromatography analysis of the mixture, it

실험 절차

4,5-di(hydroxymethyl)-1-methylcyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)-1-methylcyclohexene oxide. A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added dropwise to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir (cod) Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)-1-methylcyclohexene oxide was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 4,5-di(vinyloxymethyl)-1-methylcyclohexene oxide represented by following Formula (13) in a yield of 80%. In 1H-NMR (CDCl3) analysis, signals specific to vinyl group were observed at 6.2-6.5 ppm, 4.1-4.3 ppm, as an isomer mixture.

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