Lithium hydroxide, monohydrate → 2-Aminoterephthalic acid

HRID 1094727Notes

Reaction equation

HRID 1094727 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13]C)=[O:12])[C:5]([OH:7])=[O:6].O[Li].O>C1COCC1.CO.O>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 27248222-Aminoterephthalic acidYield 63%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-Amino-4-(methoxylcarbonyl)benzoic acid (2.5 g, 12.8 mmol) was dissolved in a mixture of THF-MeOH—H2O (40 mL, 30:5:5) and then LiOH—H2O (2 g, 64 mmol) was added. The mixture stirred at RT over night. The reaction mixture was concentrated and the residue was dissolved in 5 mL of water and then acidified with 6N HCl to pH˜3. The solid was filtered and dried to give the desired product in 63% yield.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 5 mL of water
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-43aae2f408c444f995f05a7c7bc98939
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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