反应详情

The title compound was prepared essentially according to published procedures (R. F. Borch et al., J. Org. Chem. 38 (15), 2729 (1973); Nader G. et al., French Patent 2729141 (1996)). A mixture of cyclohexane-2,3-dione monophenylhydrazone (10.1 g, 0.05 mol), diethylene glycol (25 mL) and para-toluene sulfonic acid monohydrate (11.4 g, 0.06 mol) in toluene (500 mL) was heated under nitrogen in an oil bath kept at 135° C. with water removal (Dean-Stark). After heating for 15 hours the mixture was cooled, the toluene was decanted and the tarry residue extracted three times with small portions of toluene. The combined organic phase was washed three times with saturated aqueous sodium bicarbonate, and dried over anhydrous magnesium sulfate. Removal of the solvent provided the crude title compound as a brown oil that partially solidified in vacuo (9.2 g). It was used as such in the next step. MS (ES): [M+H]+ @m/z 230.1

1. customThe title compound was prepared essentially
2. temperaturewas heated under nitrogen in an oil bath
3. customkept at 135° C. with water removal (Dean-Stark)
4. temperatureAfter heating for 15 hours the mixture
5. temperaturewas cooled
6. customthe toluene was decanted
7. extractionthe tarry residue extracted three times with small portions of toluene
8. washThe combined organic phase was washed three times with saturated aqueous sodium bicarbonate
9. dry with materialdried over anhydrous magnesium sulfate
10. customRemoval of the solvent