Sodium Hydroxide → 2-(4-Toluyl)terephthalic acid

HRID 1493847Notes

Reaction equation

HRID 1493847 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[OH-].[Na+]>CO>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([C:5]2[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[CH:12]=[CH:13][C:4]=2[C:3]([OH:21])=[O:2])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 105655[1,1'-Biphenyl]-2,5-dicarboxylic acid, 4'-methyl-, 2,5-dimethyl ester

Product 1

HCID 156614452-(4-Toluyl)terephthalic acidYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl-2-(4-toluyl)terepthalate (11.88 g) was suspended in methanol (99 ml). 5M NaOH (50 ml) was added. The reaction mixture was heated at reflux for 1.5 hours. The methanol was removed under reduced pressure. The residue was treated with ethyl acetate and water and the layers separated. The aqueous layer was washed once with ethyl acetate. The aqueous layer was then acidified with 2N HCl and extracted three times with ethyl acetate. These combined organic extracts were then dried over MgSO4, filtered and evaporated under reduced pressure gave the product (7.09 g)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. customThe methanol was removed under reduced pressure
  4. additionThe residue was treated with ethyl acetate and water
  5. customthe layers separated
  6. washThe aqueous layer was washed once with ethyl acetate
  7. extractionextracted three times with ethyl acetate
  8. dry with materialThese combined organic extracts were then dried over MgSO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-334b86a7f5c0486e8762431e2f2ea076
Source dataset
uspto-grants-1991_06
Patent number
US05025007

Reaction notes

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