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

HRID 1707989

Reaction equation

HRID 1707989 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

Dimethyl2-(4-tolyl)terephthalate (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 which 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 which

Sources & evidence

ORD record
ord-7bdac893758244e2ba0ab1b3eb9eee4c
Source dataset
uspto-grants-1994_10
Patent number
US05356889

Linked notes

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