반응 #2035934

반응 방정식

Hydrochloric acid

1,4-dimethyl-bicyclo[3.2.1]octan-3-one

trimethylorthoformate

Allyl alcohol

→

4-allyl-1,4-dimethyl-bicyclo[3.2.1]octan-3-one

수율 25.4%

용매

methanol

acetic acid

반응 조건

후처리

1. 1
   기타subsequently quenched with a NaOH solution
2. 2
   온도at reflux
3. 3
   workup.DISTILLATIONThe volatile ingredients were distilled off with a Dean Stark trap
4. 4
   세척The resulting mixture was washed with a Na2CO3 solution
5. 5
   workup.DISTILLATIONFractional distillation of the organic layer

실험 절차

Hydrochloric acid (HCl, 6 g) was added to a solution of 1,4-dimethyl-bicyclo[3.2.1]octan-3-one (400 g, 2.6 mol, obtained as above in EXAMPLE III), trimethylorthoformate (HC(OCH3)3, 280 g, 2.6 mol), and methanol (CH3OH, 400 mL). The reaction mixture was aged for 3 hours and subsequently quenched with a NaOH solution. Allyl alcohol (CH2CHCH2OH, 300 g, 5.2 mol), acetic acid (CH3COOH, 50 g), and methanesulfonic acid (CH3SO2OH, MSA, 5 g) were added and aged at reflux. The volatile ingredients were distilled off with a Dean Stark trap. The resulting mixture was washed with a Na2CO3 solution. Fractional distillation of the organic layer provided 4-allyl-1,4-dimethyl-bicyclo[3.2.1]octan-3-one (127 g) having a boiling point of 64° C. at a pressure of 0.2 mmHg.

출처