Oxygen → 4-Formylbenzoic acid

HRID 1241253

Reaction equation

HRID 1241253 reaction equation
CC1C=CC(C(O)=O)=CC=1.C(ON1C(=O)C2=CC=CC=C2C1=O)(=O)C1C=CC=CC=1.O=O.[C:33](O)(=[O:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=1>[Ti].O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C(O)(=O)C>[C:38]([C:37]1[CH:41]=[CH:42][C:34]([CH:33]=[O:43])=[CH:35][CH:36]=1)([OH:40])=[O:39]

Participants

9

Reactant 4

HCID 977OxygenHCID 7470P-Toluic Acid2×HCID 7489Terephthalic AcidHCID 7925791,3-dioxo-2,3-dihydro-1H-isoindol-2-yl benzoate

Product 1

HCID 120884-Formylbenzoic acidYield 63.2%

Reagents, catalysts & solvents 4

HCID 23963TitaniumCatalystHCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 93021Manganese acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

In a 500-ml titanium autoclave, 15.36 g (0.113 mol) of p-toluic acid, 0.301 g (1.13 mmol) of N-benzoyloxyphthalimide, 0.112 g (0.45 mmol) of cobalt(II) acetate tetrahydrate, 0.277 g (1.13 mmol) of manganese(II) acetate tetrahydrate and 104 g of acetic acid were placed, the resulting mixture was stirred at 190° C. in an atmosphere of a mixture of oxygen and nitrogen gases (1:1) [4 MPa (gauge pressure)] for 1 hour and thereby yielded terephthalic acid in a yield of 63.2% with a conversion from p-toluic acid of 67.4%. A small amount of 4-carboxybenzaldehyde was by-produced.

Sources & evidence

ORD record
ord-5af4a937228242bc882f837757e238a0
Source dataset
uspto-grants-2006_10
Patent number
US07115541B2

Linked notes

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