Acetyl chloride → 4'-Hydroxy-3',5'-dimethylacetophenone

To an ice-cooled solution of 2,6-dimethylphenol (12.2 g, 0.1 mmol) in dichloromethane, anhydrous aluminum chloride (14.4 g) was slowly added with stirring, followed by slow addition of acetyl chloride (9.4 g). The reaction mixture was stirred at 10° C. or below for 1 h, then at room temperature for 3 h. Thereafter, the mixture was poured into ice water. Then, the reaction product was extracted with dichloromethane and the extracted layer was washed with water. Further, the extracted layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized with benzene, giving the desired compound, 2,6-dimethyl-4-acetylphenol in an amount of 1.9 g.

1. additionwas slowly added
2. stirringThe reaction mixture was stirred at 10° C. or below for 1 h
3. extractionThen, the reaction product was extracted with dichloromethane
4. washthe extracted layer was washed with water
5. dry with materialFurther, the extracted layer was dried over anhydrous sodium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe residue was recrystallized with benzene

ORD record

ord-d90dacc883a040f6a4abfa92e4d0c1a4

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05594112