Propionic Acid → Acetoxybiphenylcarboxylic acid

HRID 981356Notes

Reaction equation

C(O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14](C(=O)C)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.C([O:23][C:24](=[O:26])[CH3:25])(=O)C.[C:27]([OH:31])(=[O:30])CC>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[C:24]([O:23][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][CH:5]=[CH:10][CH:9]=2)[C:16]=1[C:27]([OH:31])=[O:30])(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

345 g of 4-acetoxy-4'-acetylbiphenyl were suspended in 2.6 l of propionic acid. 2.6 g of cobalt(II) acetate, 10.1 g of manganese(II) acetate and 375 g of acetic anhydride were added to this suspension, and the mixture was heated to 110° C. The mixture was stirred for 15 minutes at 110° C., after which it was gassed with air via a valve in the base. After gassing had been carried out for 90 minutes at 110° C., the reaction was complete; the reaction mixture was discharged through the valve in the base, and the product was filtered off under suction and washed with petroleum ether. 291.3 g (84% yield) of acetoxybiphenylcarboxylic acid having a purity of 99.9% (HPLC) were obtained.

Workup

customafter which it was gassed with air via a valve in the base
waitAfter gassing had been carried out for 90 minutes at 110° C.
filtrationthe product was filtered off under suction
washwashed with petroleum ether

Sources & evidence

ORD record: ord-3bbd30e7d2204b1d8d0a3337e2f82283
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990660

Reaction notes

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