Water → 2,5-Diphenylbenzene-1,4-dicarboxylic acid

HRID 1488317Notes

Reaction equation

HRID 1488317 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)C(C)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH2:21].[Mn]([O-])(=O)(=O)=[O:23].[K+].[C:28]([O:31]CC)(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:8]1([C:6]2[C:29]([C:28]([OH:31])=[O:30])=[CH:4][C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:2]([C:1]([OH:23])=[O:21])[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 516875Potassium Permanganate2×HCID 6209841,4-dimethyl-2,5-diphenylbenzene

Product 1

HCID 111207152,5-Diphenylbenzene-1,4-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2′,5′-Dimethyl-1,1′:4′,1″-terphenyl (180.9 g) was dissolved in pyridine (4296 mL), water (405 mL) was added and the reaction mixture heated to 90° C. Potassium permanganate (KMnO4) (516 g, Sigma-Aldrich) was carefully added and refluxing continued. Additional KMnO4 (235 g) and water (677 mL) were added every 30 minutes for 2 hours. Once addition was complete, refluxing was continued for 18 hours. The reaction mixture was filtered hot through a celite pad, washing the filter cake with boiling water (3×2000 mL). The filtrates were concentrated to remove most of the pyridine before adjusting to pH-1 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water (2×1400 mL) and dried to give a cream solid. The solid was then refluxed in ethyl acetate (840 mL), cooled, collected by vacuum filtration and washed with ethyl acetate (2×233 mL) to give the product as a cream solid. Yield; 183.8 g.

Workup

  1. temperaturerefluxing
  2. additionOnce addition
  3. temperaturerefluxing
  4. filtrationThe reaction mixture was filtered hot through a celite pad
  5. washwashing the filter cake with boiling water (3×2000 mL)
  6. concentrationThe filtrates were concentrated
  7. customto remove most of the pyridine
  8. filtrationThe solids were collected by vacuum filtration
  9. washwashed with water (2×1400 mL)
  10. customdried
  11. customto give a cream solid
  12. temperaturecooled
  13. filtrationcollected by vacuum filtration
  14. washwashed with ethyl acetate (2×233 mL)

Sources & evidence

ORD record
ord-8180bb1d307145b7a793c80dab00d31d
Source dataset
uspto-grants-2016_08
Patent number
US09431145B2

Reaction notes

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