Methanol → 4-Carbamoylbenzoic acid

HRID 1177977Notes

Reaction equation

HRID 1177977 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.CO.O>C1COCC1>[C:5]([OH:15])(=[O:4])[C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 596094Methyl 4-carbamoylbenzoate

Product 1

HCID 5060574-Carbamoylbenzoic acidYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (26 mg, 0.6 mmol) was added to a stirred solution of terephthalamic acid methyl ester (73 mg, 0.41 mmol) in THF:MeOH:water mixture (3:1:1, 1 mL) and the resulting mixture was stirred at room temperature overnight. The THF and MeOH were then evaporated and the resulting residue was acidified to pH 2 using 10% citric acid solution. The product was extracted using EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 30 mg (53.6% yield) of terephthalamic acid. LCMS Purity: 92.2%.

Workup

  1. customThe THF and MeOH were then evaporated
  2. extractionThe product was extracted
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ce316b608154dbe92ba5845e55d03da
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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