路易斯酸催化下，对位取代的酚和CCl4进行Friedel–Crafts反应得到环己二烯酮的反应。

反应机理

反应实例

4-Methyl-4-trichloromethyl-2,5-cyclohexadienone (2). To powdered anhyd AlCl3 (8.33 g, 0.063 mol) in 25 mL CS2 was added 5.4 g (0.05 mol) of distilled p-cresol 1 in 5 mL carbon disulfide with stirring, over 15 min (evolution of HCl). Distilled CCl4 (7.70 g, 0.050 mol) was added and the mixture was heated to 45 ℃, while a brown tar collected on the sides of the flask. After 2 h of heating

and evaporation, H2O was added dropwise. Steam-distillation afforded 6.9 g of 2; 6.8 g, 60%, mp 103.8–104 ℃ on crystallization (PE).

【Newman MS, J Org Chem., 1954, 19, 978】

相关文献

1 Zincke Th, Suhl R Chem Ber 1906 39 4148

2 Newman MS J Org Chem 1954 19 978

3 Newman MS J Org Chem 1958 23 1236

4 Newman MS J Am Chem Soc 1959 81 6454

5 Newman MS J Ind Chem Soc 1974 51 95

6 Sergeev SV Russ Chem Bull 1988 37 790

7 Coleman RS Org Lett 2000 2 277

8 Firouzabadi H Bull Chem Soc Jpn 2002 75 2195

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 542-543.