Sodium Carbonate → 4-(Pyridin-4-yl)benzoic acid

HRID 1937045Notes

Reaction equation

[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].[C:7]1(C)[CH:12]=[CH:11][C:10]([CH:13]2[CH:18]=[CH:17][N:16](C(=O)C(C)(C)C)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[Mn]([O-])(=O)(=O)=O.[K+].[Mn]([O-])(=O)(=O)=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[C:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:11][CH:12]=1)([OH:2])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

1.0 g of anhydrous sodium carbonate, 0.05 g of benzyltributylammonium chloride and 0.8 g of 4-p-tolyl-N-pivaloyldihydropyridine are added at room temperature to 75 ml of a 2% strength by weight aqueous potassium permanganate solution. After stirring at 100° C. for 1.5 hours, excess permanganate is reduced by means of sodium dithionite, the precipitated manganese dioxide is filtered off, the filtrate is acidified and the precipitated product is filtered off to give 4-(4′-carboxyphenyl)-pyridine in a yield of 81%.

Workup

filtrationthe precipitated manganese dioxide is filtered off
filtrationthe precipitated product is filtered off

Sources & evidence

ORD record: ord-5bc590703a2e446295014ea98f2954f4
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392051B2

Reaction notes

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