Reaction #1328439

ord-8093fb3a85fd4a7898266b022ea0f36c

Reaction equation

CC(C)c1ccccc1
isopropylbenzene
CC(=O)ON1C(=O)c2ccccc2C1=O
N-acetoxyphthalimide
O=O
oxygen
→
CC(=O)c1ccccc1
acetophenone
CC(C)(O)c1ccccc1
2-phenyl-2-propanol
O=C(O)c1ccccc1
benzoic acid

Reactants

CC(C)c1ccccc1
isopropylbenzene
CC(=O)ON1C(=O)c2ccccc2C1=O
N-acetoxyphthalimide
O=O
oxygen

Reagents

CC(=O)[O-].CC(=O)[O-].O.O.O.O.[Co+2]
cobalt(II) acetate tetrahydrate
CC(=O)[O-].CC(=O)[O-].O.O.O.O.[Mn+2]
manganese(II) acetate tetrahydrate

Solvents

CC(=O)O
acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A mixture of 1.202 g (10 mmol) of isopropylbenzene, 0.205 g (1 mmol) of N-acetoxyphthalimide, 0.025 g (0.1 mmol) of cobalt(II) acetate tetrahydrate, 0.025 g (0.1 mmol) of manganese(II) acetate tetrahydrate and 15 ml of acetic acid was stirred at 100° C. in an atmosphere of oxygen gas (1 atm=0.1 MPa) for 2 hours and thereby yielded benzoic acid, acetophenone and 2-phenyl-2-propanol in yields of 5%, 30% and 12% (analyzed by gas chromatography), respectively, with a conversion from isopropylbenzene of 59%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07115541B2uspto-grants-2006_10