Dichloromethane → 1-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Temperature

0 °C

Acetyl chloride (287 g) was added to a mixture of aluminum chloride (488 g) and methylene chloride (1.8 l) at −60° C. while stirring. 2-tert-Butylphenol (500 g) was added at −70° C. to −50° C. over a period of 1.5 hours, and the temperature was then raised to 0° C. The reaction mixture was poured into ice and extraction was performed with ethyl acetate. The organic layer was washed with brine, the solvent was distilled off under reduced pressure, methanol (1 l) and potassium carbonate (300 g) were added to the residue and the mixture was stirred at room temperature for 2 hours. After adding water to the reaction mixture and neutralizing it with concentrated hydrochloric acid, extraction was performed with ethyl acetate and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane was added to the residue and the resulting crystals were filtered off to yield the title compound (352 g) as white crystals.

1. additionThe reaction mixture was poured into ice and extraction
2. washThe organic layer was washed with brine
3. distillationthe solvent was distilled off under reduced pressure, methanol (1 l) and potassium carbonate (300 g)
4. additionwere added to the residue
5. stirringthe mixture was stirred at room temperature for 2 hours
6. additionAfter adding water to the reaction mixture and neutralizing it
7. extractionwith concentrated hydrochloric acid, extraction
8. washthe organic layer was washed with brine
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. additionHexane was added to the residue
12. filtrationthe resulting crystals were filtered off

ORD record

ord-5e2b43b56cd546868be683f6e0040944

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07244730B2