p-Toluenesulfonic acid → Cyclohexanone, 3,3-dimethyl-

Temperature

85 °C

9.260 g of 5% Pd/C were placed in a 2 L glass-steel autoclave with glass-liner. 65 g of dimedone, 146 mL of isopropanol and 2.580 g of p-toluene sulfonic acid were added. The glass-liner was closed and stirring was started with 500 rpm. The autoclave was flushed three times with 5 bara N2. The stirrer was turned off and the autoclave was pressurized with 5 bara H2 for 10 minutes for pressure check. The pressure was released. The stirrer was turned on again to 500 rpm and the autoclave was heated to 85° C. internal temperature. The autoclave was pressurized with 2 bara H2 and the stirrer was set to 1000 rpm. The reaction mixture was stirred under 2 bara H2 at 85° C. until 123% of the theoretical H2-amount had been consumed. Then stirring was slowed to 500 rpm, the autoclave was cooled to an internal temperature below 25° C. and depressurized. After three times flushing with N2 at 5 bara for 100 minutes stirring was stopped and the autoclave was opened. The content was sucked and filtrated over a 0.45 μm filter. A 30 mL filtrated sample was diluted with 1 mL of isopropanol and 5 mg of NaHCO3 and then analyzed by GC.

1. customThe glass-liner was closed
2. customThe autoclave was flushed three times with 5 bara N2
3. stirringThe reaction mixture was stirred under 2 bara H2 at 85° C. until 123% of the theoretical H2-amount
4. customhad been consumed
5. stirringThen stirring
6. temperaturethe autoclave was cooled to an internal temperature below 25° C.
7. customAfter three times flushing with N2 at 5 bara for 100 minutes
8. stirringstirring
9. filtrationfiltrated over a 0.45 μm
10. filtrationfilter
11. filtrationA 30 mL filtrated sample
12. additionwas diluted with 1 mL of isopropanol and 5 mg of NaHCO3

ORD record

ord-5edf2a96c27f49faad9c38f5e5b1999b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674143B2