反应详情

温度

-10 °C

Aluminum chloride (26.6 g, 200 mmol) was added to chlorobenzene (40 mL), and the mixture was cooled to −10° C. A solution of 2-tert-butyl-5-methylphenol (16.4 g, 100 mmol) in triethyl orthoformate (32.5 g, 220 mmol) was added dropwise. When addition was complete, the reaction mixture was warmed to 0° C. to 5° C. and kept at that temperature for 6 hours. Five percent HCl (100 mL) was added, and the mixture was extracted with 1:1 EtOAC:toluene. The organic phase was extracted with 23% KOH (3×50 mL) and water (25 mL), and the water extract was combined with the KOH extracts. The pH of the combined aqueous extracts was adjusted to 4 with 37% HCl. The resulting precipitate was filtered, washed with water (3×50 mL), and dried to give the title compound, mp 171-171° C.

1. additionWhen addition
2. temperaturethe reaction mixture was warmed to 0° C. to 5° C.
3. extractionthe mixture was extracted with 1:1 EtOAC
4. extractionThe organic phase was extracted with 23% KOH (3×50 mL) and water (25 mL)
5. extractionthe water extract
6. filtrationThe resulting precipitate was filtered
7. washwashed with water (3×50 mL)
8. customdried