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ChemicalBook CAS DataBase List NOOTKATONE
4674-50-4

NOOTKATONE synthesis

1synthesis methods
By oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.
-

Yield:-

Steps:

Multi-step reaction with 8 steps
1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C
2: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
4: 81 percent / TiCl4 / CH2Cl2
5: 71 percent / NaNH2 / benzene
6: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
8: Al2O3 / hexane / 24 h / 60 °C

References:

Yanami, Tetsuji;Miyashita, Masaaki;Yoshikoshi, Akira [Journal of Organic Chemistry,1980,vol. 45,# 4,p. 607 - 612]

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