Tert-Butylbenzene → 1-(4-T-Butylphenyl)-3-chloropropan-1-one

Temperature

0 °C

To aluminum chloride (29.33 g, 220 mmol) in dichloromethane (300 mL) at 0° C. with stirring was added dropwise a solution of t-butyl benzene (31 mL, 200 mmol) and 3-chloropropionyl chloride (19 mL, 200 mmol) in dichloromethane. After the addition was complete, the reaction mixture was stirred from 0° C. to room temperature overnight. Then next morning, TLC indicated that all of the t-butyl benzene was consumed, and the reaction mixture was cooled to 0° C. With stirring, water (about 120 mL) in a dropwise fashion until the effervescence ceased. Finally, the layers were separated, and the organic layer was washed with water (3×150 mL) and then brine (1×150 mL). The dichloromethane layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a light tan powder (45.6 g).

1. additionAfter the addition
2. customwas consumed
3. stirringWith stirring
4. customFinally, the layers were separated
5. washthe organic layer was washed with water (3×150 mL)
6. dry with materialThe dichloromethane layer was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-6940f6746b8141b2af292c3e5801408f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299077B2